TW200422377A - Novel polymers for use in optical devices - Google Patents

Abstract

The present invention relates to polymers comprising diazine, especially pyrimidine, containing repeating units. Optical devices, comprising the polymers of the present invention, can show significant advantages in color purity, device efficiency and/or operational lifetime. In addition, the polymers can have good solubility characteristics and relatively high glass transition temperatures, which facilitates their fabrication into coatings and films that are relatively thin, thermally stable, and relatively free of defects.

Description

2004223 77 发明 Description of the invention: H j ^ fr ^ 1 The present invention relates to novel polymers containing repeating units containing pyrimidines, and to optical devices such as those containing electroluminescent devices or photovoltaic devices. ). I: Prior art] Poly (p-phenylene vinylene) derivatives have been known as electroluminescence (EL) materials for some time (see, for example, WO90 / 13148). WO98 / 11150 reveals chemical formula

Triazine polymer 10 and its use in electroluminescence (EL) configurations. US-A-5,876,864 relates to fluorene-based alternating polymers and their use as electroluminescent materials. Vysokomolekulyarnye Soedin · M. M. Koten et al .; Seriya B: Kratkie Soobshcheniya, Vol. 30, No. 10, 1978, 15 792-793 discloses 2-phenyl-4,6_bis (p-aminophenyl) ) Pyrimidine:

Main polyimide, where R is the base of the following chemical formula 2004223 77 J 1

DE-A-10143353 discloses a conjugated polymer containing a helical difluorene unit and a selective pyrimidine-based unit of the following chemical formula

10 and its use as an electroluminescent material. US2001 / 0012572 discloses the polymerization of pyrimidine-containing units of the following chemical formula: 2004223 77 SCH2CH (CH2CH3) CH2CH2CH2CH3

N people N

(Mw = 23000)

(Mw = 28000)

, And WOOO / 46321 and 1 ^ 4-6,512,083 are related to rhenium-containing polymers and their use in electroluminescent configurations. EP-A-690052 reveals the use of such as

A total of 10 polymers with mouth bites were used as electroluminescent materials. E -Ar-Ar ~ y ^ -Ar-Ar-E Nv Ν W002 / 059121 discloses a monomer having a chemical formula ^, wherein X is 0, S, NR, RC-CR, or ROCR, Ar is aryl or hetero Aryl, and E is a reactive group capable of chain extension, and its use in the manufacture of polymers that can be used in optical devices (see also WO01 / 62869). 15 DE-A_19651439 (US-A-6,323,373) is a polymerizable bisaryl derivative of the following chemical formula 2004223 77

Ring 2 Ring 1 The symbols and signs in it have the following meanings: 5 X: -CH2-Z, -CHO; Y1, Y2, Y3: CH; N, Z: same or different, I, Cl, Br, CN, SCN, NCO, PCHOR1). PO (R2) 2, P (R3), a-; aryl: aryl having 6 to 14 carbon atoms; 10 R ', R ": same or different, CN, F, C1, having 1 to 20 Linear or branched or cyclic alkyl or alkoxy groups of one carbon atom, wherein one or more non-adjacent CH2 groups are optionally _〇_, _s_, _C0_, -C〇〇_, _〇_c〇 ·, -NR4_,-(NR5r6) + A- or -CONR7-, and one or more H atoms are optionally substituted with F, or an aryl group having 6 to 14 carbon atoms, which may be R ', R2, R3, R5, R6: the same or different, aliphatic or aromatic hydrocarbon groups having 1 to 20 carbon atoms; R4' R7: the same or Dissimilar, hydrogen or aliphatic or aromatic nicotinic group having 1 to 20 carbon atoms; 20 Δ-. ^ • an earlier charged anion or its equivalent; m: 0, 1 or 2; n: L 2 , 3, 4 or 5, and its use in the manufacture of polymers. When it comes to performance compared to existing technologies, bowing into organic electroluminescence displays has many challenges. Need to use special guidelines (ie, .o to get the correct color coordinates is already a problem. When compared to existing inorganic technology, electro-fabrication = device operating life is relatively low. In addition, manufacturing with pure blue and long odd Material is one of the major problems used in this industry. [Summary of the Invention] Therefore, the object of the present invention is to provide novel materials that, when incorporated in optical devices, show significant color purity, device efficiency, and / or operating life. Advantages. This object is solved by the polymer of the present invention, which includes repeating units containing a diazine (especially a pyrimidine). An optical device including the polymer of the present invention can show significant advantages in color purity, device efficiency, and / or operating life. In addition, the polymer has good dissolution characteristics and a relatively high glass transition temperature, which facilitates its production into coatings and films that are relatively thin, thermally stable, and relatively free of defects. If the polymer contains end groups that can be cross-linked, After the film or coating is formed, the crosslinking of these groups increases its solvent resistance, during which more layers of solvent-based materials are deposited. The application is advantageous. Therefore, the polymer of the present invention needs to have a glass transition temperature higher than 100 °, especially a glass transition temperature higher than 150 ° c. When used herein, "the polymer of the present invention The term refers to a polymer with a repeating order 2004223 77 yuan of chemical formula Ϊ (comprising chemical formulas la and lb) and / or π (comprising chemical formulas Ila, lib and lie). In a first aspect, the present invention relates to a polymer containing the following chemical formula Polymer of the heavy element >

R

(1), wherein R1 and R2 are each independently an organic substituent, particularly a cvQo square group or a c ^ c: 26 heteroaryl group, which may be optionally substituted,

X1 and X2 are each a divalent bond group, wherein, the chemical formula

(la) or

(lb) is better for repeated early elements. 10 Examples of suitable divalent bonding groups χΐ and X2 are single bonds, -CO-, _COO_;

10 2004 223 77

11 2004 223 77

nl, n2, n3, n4, n5, n6 and n7 are integers from 1 to 10, especially from 1 to 3, R6 and R7 are each independently H, CrC18 alkyl, substituted by E and / or D 5 interrupted CrC18 Alkyl, C5-C12 cycloalkyl, substituted with E (: 5-(: 12 cycloalkyl, C6-C24 aryl, E substituted C6-C24 aryl, C2-C2G heteroaryl, E Substituted C2-C2 () heteroaryl, C2-C18 alkenyl, C2-C18 alkynyl, CrC18 alkoxy, substituted with E and / or interrupted by D (^-(: 18 alkoxy, C7_C25 aryl Alkyl, or -CO-R28, 10 R8 CrC18 alkyl, CrC18 alkyl substituted with E and / or D interrupted, C6-C24 aryl, or C7-C25 * alkyl, R9 and R1G are each independently CrCls alkyl, ci_C18 alkyl substituted with E and / or D interrupted, C6-C24 aryl, C6-C24 aryl substituted with E, C2-C20 heteroaryl, C2-C2G heteroaryl substituted with E Group, C2-C18 alkenyl group, (: 2 < 18 alkynyl 15 group, crci8 alkoxy group, crC18 alkoxy group substituted with E and / or D interruption, or C7-C25 aralkyl group, or R9 and R1G Ring, especially a five- or six-membered ring, which may be optionally substituted with R6, R14 and R15 are each independently H, CVCm alkyl, substituted with E and / or D 20 Broken ci_ci8 alkyl group, CfC24 aryl group, c6-C24 aryl group substituted with E, heteroaryl group, or c2-C2G heteroaryl group substituted with E, D is -CO-; -COO-; -S-; -SO-; -SOr; -NR25-; -SiR3〇R31-; 12 2004223 77 -POR32-; -CR23 = CR24-; or -OC-; and E system -OR29; -SR29; -NR25R26; -COR28; _COOR27; -CONR25R26; • CN; -OCOOR27; or halogen; wherein, R23, R24, R25 and R26 are each H; C6_C18 aryl; C6 substituted with (^ -〇: 18 alkyl 5 group, CrC18 alkoxy group -C18 aryl; CrC18 alkyl; or intermittent CrC18 alkyl; or R25 and R26 together to form a five- or six-membered ring, especially

R27 and R28 are each independently H; C6_C18 aryl; c6_c18 aryl substituted with CVC18 alkyl, or 10 crc18 alkoxy; crc18 alkyl; or crc18 alkyl interrupted by · 〇_, R29 is H; C6- C18 aryl group; c6-c18 aryl group substituted with CrC18 alkyl group, CrC18 alkoxy group; CrC18 alkyl group; or CVC18 alkyl group with -0 interruption, R30 and R31 are each CrC18 alkyl group, C6-C18 aromatic group Group, or C6-C18 square group substituted with CrC18 15 alkyl group, and R32 is CrC18 alkyl group, C6-C18 aryl group, or C6_c18 aryl group substituted with CrC18 alkyl group. Preferably, R6 and R7 are each H, CVC18 alkyl, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, second butyl, third 20 butyl , 2-methylbutyl, n-pentyl, isopentyl, n-hexyl, 2-ethylhexyl, or n-heptyl, CrC18 alkyl substituted with E and / or D interrupted, such as -ch2och3,- ch2och2ch3, -ch2och2ch2och3, or 13 2004223 77 • CH2OCH2CH2OCH2CH3, c6_c24 alkyl, such as phenyl, naphthyl, or biphenyl, C5-C12 cycloalkyl, such as cyclohexyl, C6-C24 aryl substituted with E , Such as -c6h4och3, -c6h4och2ch3, -c6h3 (och3) 2, or -c6h3 (och2ch3) 2, -c6h4ch3, -c6h3 (ch3) 2, -c6h2 (ch3) 3, 5 or -C6H4tBu. R is preferably an alkyl group such as' methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, second butyl, third butyl, 2-methylbutyl, n-pentyl Group, isopentyl, n-hexyl, 2.ethylhexyl, n-heptyl, or c6-C24 aryl, such as phenyl, naphthyl, or biphenyl. 10 Preferably, R9 and R1G are each h, c, c18 alkyl, such as n-butyl, second butyl, hexyl, octyl, or 2-ethyl-hexyl, substituted with e and / or D intermittent CrC18 alkyl, such as -CH2 (OCH2CH2) wOCH3, W = 1, 2, 3, or 4, C6-C24 aryl, such as phenyl, naphthyl, or biphenyl, substituted with E C6-C24 aryl, 15 such as -C6H4OCH3, · 0: 6Η400: Η2 (: Η3, -c6h3 (〇ch3) 25 -c6H3 (〇ch2ch3) 2? -C6h4ch35 -C6H3 (CH3) 25 -C6H2 (CH3 ) 3, or _C6H4tBu, or R9 and R1g together to form a 4- to 8-membered ring, especially a 5- or 6-membered ring, such as cyclohexyl, or cyclopentyl, which can be optionally substituted with CrC8 alkyl 2〇 Preferably, R14 '& R15' are each independently H, alkyl, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, or second butyl Or C6-Cm aryl, such as phenyl, naphthyl, or biphenyl. D is preferably -CO-, -COO ·, -S-, -SO-, -SOr, -0, _NR ', R25 is a crCl8 alkyl group such as methyl, ethyl, n-propyl, isopropyl, ^ 14 2004223 77 butyl, isobutyl, Or a second butyl, or a C6-C24 aryl, such as phenyl, naphthyl, or biphenyl. E is preferably -OR29; -SR29-nr25r25; c〇r28; -CONRf; or -CN; wherein, r25 , r27, ... and ... are each independently & 5 Cis alkyl groups such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, second butyl, hexyl, octyl, Or 2-ethyl-hexyl, or kb aryl, such as phenyl, naphthyl, or biphenyl. Among the above X1 and X2 groups, the following groups are preferred:

R1 and R2 may in principle be any organic substituent, as long as it has no negative effect on the electroluminescent properties of the polymer. ... and examples of R2 are H, Ci < ^ alkyl, CrCi8 alkyl substituted with E and / or D interrupted, C2_Ci8 alkenyl, 15 C2_C18 alkynyl, CrC18 alkyloxy, substituted with E and / or D Intermittent C18 alkoxy, C7-C25 aralkyl,

-X5

Cm aryl, or CVC2. Heteroaryl, which may be optionally substituted, in particular, a radical of the following formula 15 2004223 77

16 2004 223 77

Where 'ml, m2, m3, m4, m5, m6 and m7 are integers from 1 to 10, especially from 1 to 3, X6 is H, CrC18 alkyl, CrC18 alkyl 5 substituted with e and / or D interrupted CrC24 aryl, its selectivity can be substituted, especially

C2-C18 alkenyl, c2_C18 alkynyl, CrC18 alkoxy, CrC18 alkoxy substituted with D and / or D interrupted, or CrC25 * alkyl, 10 χ4 Ci_C18 alkyl, substituted with E and / or D intermittent CrC18 alkyl, aryl, which can be substituted, χ5 is Crci8 alkyl, C6-C24 aryl, C6-C24 aryl substituted with -0CrC18 alkyl, or -〇C6-C24 aryl base,

Rl1, R12, and R13 are each H, C, C18 alkyl, Crci8 alkyl substituted with E and / or 15 interrupted by D, C6_C24 aryl, C6-C24 aryl substituted with E, C2_ci8 alkenyl, C2 -C18 alkynyl, CrC18 alkoxy, substituted with E and / 17 2004223 77 or CrC18 alkoxy interrupted by D, C7_C25 aralkyl, and D, E, R6, R7, R8, R9, R10, Rl4 'And R15 are as defined above. Preferably, R6 and R7 are each independently H, c, Ci8 alkyl, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl , Second butyl, fifth dibutyl, 2-methylbutyl, n-pentyl, isopentyl, n-hexyl, 2-ethylhexyl, or n-heptyl, substituted with E and / or interrupted by d CrC18 alkyl, such as -CH2OCH3, -CH2〇CH2CH3, · ΟΗ2Ο0Ή2αί2Ο (: Η3, or -CH2OCH2CH2OCH2CH3, C5-C12 cycloalkyl, such as, cyclohexyl, CrC24 aryl, such as, phenyl, naphthyl, or Biphenyl, 10 c6-c24 aryl substituted with E, such as · 〇6Η4 (χ: Η3, T6Η4〇σΗ2 (: Η3, -C6H3 (OCH3) 2, or -C6H3 (OCH2CH3) 2, -C6H4CH3, -C6H3 (CH3) 2, _C6H2 (CH3) 3, or -C6H4tBu. R8 is more H, CrC18 alkyl, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, second butyl, third butyl, 2-methylbutyl, n-pentyl 15-based, iso-pentyl, n-hexyl, 2.ethylhexyl, and n-heptyl, or C6-C24 aryl, such as phenyl, naphthyl, or biphenyl. Preferably, R9 and R1G are each separate H, C, C18 alkyl, such as n-butyl, first butyl, hexyl, octyl, and 2-ethyl-hexyl, CVC18 alkyl substituted with E and / or D interrupted, such as 20 , -CH2 (OCH2CH2) wOCH3, W = 1, 2, 3, or 4, C6-C24 aryl, such as phenyl, naphthyl, and biphenyl, C6-C24 aryl substituted with E, such as, -C6H4OCH3, -C6H4OCH2CH3, -c6h3 (och3) 2, -c6h3 (och2ch3) 2, -c6h4ch3, -c6h3 (ch3) 2, -C6H2 (CH3) 3, and -C6H4tBu, or R9 and r1g together The clothes of 8 members and 18 members are especially rings of 5 or 6 members, such as cyclohexyl, or cyclopentyl, which can be optionally substituted by Crc8 alkyl groups. Chedi, 玟 14 'and Rl5' are each independently related to each other. H, CrC18 alkyl, such as methyl'ethyl, n-propyl, isopropyl, n-butyl Isobutyl, and sec-butyl, or 5 C24 aryl group, such as phenyl, naphthyl and biphenyl. Che Jia Jia CrC18 alkyl, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, second butyl, third butyl, hexyl, octyl, and 2- Ethyl-hexyl, or kC24 aryl, such as phenyl, naphthyl, and biphenyl, and π is preferably CrCl8 alkyl, such as methyl, ethyl, n-propyl, isopropyl, n-butyl Methyl, isobutyl 10yl, second butyl, third butyl, hexyl, octyl, and 2-ethylhexyl, or C6-C24 aryl, such as phenyl, naphthyl, and biphenyl. Preferably, R11, R12 and R13 are each H, CVC18 alkyl, such as fluorenyl, and ethyl, CrC18 alkyl substituted with E and / or D interrupted, such as -ch2och3, -ch2och2ch3,- ch2och2ch2och3, 15 and -CH20CH2CH20CH2CH3, c6-c24 aryl, such as phenyl, naphthyl, and biphenyl, C6-C24 aryl substituted with E, such as -C6H4OCH3, -c6h4och2ch35 -c6h3 (〇ch3) 25 -c6h3 (〇ch2ch3) 2? -c6h4ch3? C6H3 (CH3) 2, -C6H2 (CH3) 3, and -C6H4tBu, C2-C18 alkenyl, C2-C18 alkynyl, CrC18 alkoxy, substituted with E and // Or CrC18 alkoxy 20 groups interrupted by D, such as _OCH2OCH3, -OCH2OCH2CH3, CH2OCH2CH2OCH3, -OCH2CH2OCH3, -OCH2CH2OCH2CH2OCH3 and -OCH2CH2OCH3, -OCH2CH2OCH2, methoxy, ethoxy, n-butoxy, n-butoxy Group, isobutoxy, second butoxy, hexyloxy, octyloxy, and 2-ethyl-hexyloxy, and CrC25 aryloxy. 19 2004223 77 D is more preferably -CO-, -COCK-S-, -SO-, -S02-, -〇-, -NR25-, wherein 'R is C, C18 alkyl, such as methyl, ethyl , N-propyl, isopropyl, n-butyl, isobutyl, second butyl, third butyl, hexyl, octyl, and 2-ethyl-hexyl, or square groups such as phenyl, naphthalene And biphenyl. E is preferably OR2, _SR29, _NR25R25, _C〇R28, _c〇〇r27,

-CONR25R25, or _CN, where R25, R27, R28, and R29 are each a CrCls alkyl group, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, first butyl Radicals, hexyl, octyl, 2-ethylhexyl, or C6-C24 aryl, such as phenyl, heptyl, and biphenyl. Preferably, at least one of R1 and R2 is a C6-C24 aryl group or a C2-C2Q heteroaryl group, which may be optionally substituted. In this case, R1 and R2 are preferably selected from

R6, R7 and X6 are each H, CrC18 alkyl, such as methyl, ethyl, n

15 Propyl, isopropyl, n-butyl, isobutyl, second butyl, third butyl, hexyl, octyl, 2-ethyl-hexyl, CrC18 alkyl substituted with E and / or D interrupted Groups such as -ch2och3, -ch2och2ch3, -ch2och2ch2och3, and -ch2och2ch2och2ch3, c6_c24 aryl groups, such as phenyl, naphthyl, and biphenyl, C6-C24 aryl groups substituted with E, such as -C6H4OCH3, 20 -c6h4och2ch35 -c6h3 (〇ch3) 2? -c6h3 (〇ch2ch3) 25 -c6h4ch35 20 2004223 77 -C6H3 (CH3) 2, -C6H2 (CH3) 3, and -C6H4tBu, R8 series H, C "C18 alkyl, Such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, and second butyl, or c6-c24 aryl, such as phenyl, naphthyl, and biphenyl, and 5 ^ And R1G are each H, CrC18 alkyl, such as n-butyl, second butyl, hexyl, octyl, or 2-ethyl-hexyl, cvc18 alkyl substituted with E and / or D interrupted, For example, _CH2 (〇CH2CH2) woCH3, w = I 2,3, or 4, C6_C: 24 aryl, such as phenyl, naphthyl, or biphenyl, aryl substituted with E, such as _C6H4OCH3 , _C6H4OCH2CH3, _C6H3 (OCH3) 2, 10 -C6H 3 (OCH2CH3) 2? .C6H4CH3? -C6H3 (CH3) 2? -C6H2 (CH3) 35 or -QHjBu, or R9 and rig together form a 4 to 8 member ring, especially a 5 or 6 member ring, such as, Cyclohexyl, or cyclopentyl. Most preferably, in the chemical formula and Ib, R2 is H and C6_C24 aryl or C2-C2G heteroaryl. 15 The polymer of the present invention contains 0-5 mole% to 100 moles. Mol% (especially 40 mol% to 60 mol%) of the repeating unit of formula I, wherein the sum of all repeating units (monomers) is mol%. Therefore, the polymer of the present invention In addition to the repeating unit of Chemical Formula 1, it may further include a comonomer in an amount of up to 99-5 mol% (especially in an amount of 60 mol% to 40 mol%). 20 In a preferred embodiment of the present invention, polymerization A homopolymer of a system comprising a repeating unit of the following chemical formula: 21 2004223 77 R1 N human NljSf ^ x2

(Ia), or (lb) where

, Or r \

Rb R °

In particular W, or

ΧΌ, or 5, where X6 is H, CrC18 alkyl, cyclohexyl, or (^ -018 alkoxy, R2 is H,

X1 and X2 are each independently a base of the following chemical formula

Polymers of the invention not having the following chemical formula 22 10 2004 223 77

23 2004 223 77 SCH2CH (CH2CH3) CH2CH2CH2CH3

N people N

(Mw = 23000)

(Mw = 28000)

Preferably, the present invention does not include a repeating unit of the following chemical formula

Among them, X (= X), Y (= Z), Y1 (= R1), Y2 (= R2), X (= η) and y (= m) are as defined in DE-A-10143353. A suitable comonomer T is selected from the group consisting of

24 10 200422377

25 200422377

5 wherein, R16 is H; C6-C18 aryl, aryl substituted with CrC18 alkyl, c "c18 alkyl, c7-c25 aryl, or -0-interrupted Cl-Cl8 alkyl; p Is an integer from 1 to ίο, in particular 1,2 $ 3, q is an integer from 1 to ίο, especially 1,2 or 3, 10 s is an integer from 1 to 10, especially 1,2 or 3, R6, R7, R8, R9 and R1G are as defined above, or R9 and R10 together form a base of the formula ^ CRWOR1.1, wherein R10G and R1G1 are each H, CrC18 alkyl, each substituted by E and / or interrupted by D CrCls, C6-C24 aryl, C6-C24 aryl substituted with E, 15 CrC2G heteroaryl, or C2-C2G heteroaryl substituted with E, and 26 422377 R4 and R15 are each H, Ci_Ci8 alkyl, eve "alkyl substituted with E and / or D interrupted, c0-C24 aryl, C6-C24 aryl substituted with E, crC20 heteroaryl, or C2_Cm heteroaryl substituted with E . If R9 and R1G form the formula = criggri (h, T is preferably the following formula

Among them, HR103 is C18 aryl group, Cl-Cl8 oxygen group: CA. Aryl, Q-q. Aryloxy, or bis (CrCi8) amine, wherein 10 aryl or aryloxy can be optionally substituted with C-CJ groups (purchased. 6,512,083). A good example of T is selected from the following chemical formula

6

27 2004 223 77

R and R7 are each independently H, alkyl, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, second butyl, third butyl, and 2.methylbutyl , 5 n-pentyl, iso-pentyl, n-hexyl, 2 · ethylhexyl, or n-heptyl, substituted with E and / or interrupted 2CrC18 alkyl such as -CH20CH3, -CH20CH2CH3, -ch2och2ch2och3, or -ch2och2ch2och2ch3, 0: 5 < 12 rings

Alkyl, such as cyclohexyl, c6-c24 aryl, such as phenyl, naphthyl, or biphenyl, C6-C24 aryl substituted with E, such as -C6H4OCH3, 10 -C6H4OCH2CH3, -C6H3 (OCH3) 25 Or _C6H3 (OCH2CH3) 2, -C6H4CH3, -C6H3 (CH3) 2, _C6H2 (CH3) 3, or _C6H4tBii, R is H, CpCu alkyl, such as' methyl, ethyl, n-propyl, isopropyl Base, n-butyl, isobutyl, second butyl, third butyl, 2-methylbutyl, n-pentyl, isopentyl, n-hexyl, 2-ethylhexyl, n-heptyl, or c6 -C24 aryl, such as phenyl, naphthyl, 15 or biphenyl, and R9 and R1G are each H, CrC18 alkyl, such as n-butyl, second butyl, hexyl, octyl, or 2 -Ethylhexyl, CrC18 alkyl substituted with E and / or D interrupted, such as, -CH2 (0CH2CH2) w0CH3, w = 1, 2, 3, or 4, 28 2004223 77 G-C24 aryl, such as, Phenyl, naphthyl, or biphenyl, c6_c24 aryl substituted with E, such as -C6H4OCH3, -c6h4och2ch3, -c6h3 (och3) 2, -c6h3 (och2ch3) 2, -c6h4ch3, -c6h3 (ch3) 2 , -C6h2 (ch3) 3, or -QHjBu, or R9 and Ri❹ together form a 4 to 8 member ring, especially 5 5 or 6 membered rings, such as cyclohexyl, or cyclopentyl, which may optionally be cr cls (such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, Second butyl, third butyl, 2-methylbutyl, n-pentyl, isopentyl, n-hexyl, ethylhexyl, or n-heptyl) alkyl substituted, substituted with E and / or interrupted by d Ci_Ci8 alkyl, such as -CH2OCH3, -CH2OCH2CH3, 10 -CH2OCH2CH2OCH3, or -CH20CH2CH20CH2CH3, C ^ C24 aryl, such as phenyl, naphthyl, or biphenyl, cc substituted by e

Aryl groups such as -c6h4och3, -c6h4och2ch3? -C6h3 (〇ch3) I or -C6H3 (〇CH2CH3) 2, -C6H4CH3, -C6H3 (CH3k ^ or _C6H4tBu ○ 15 In preferred embodiments, the polymer contains a chemical formula ia or 7 complex-han-yuan, where R1 is the base of the formula

29 200422377 R2 is R, R6 and R7 are each independently R, CVC12 alkyl, cyclohexyl, or C "C12 alkoxy, R8 is crc18 alkyl, cvc18 alkyl interrupted by one or two oxygen atoms, or C6_C12 Aryl, which may be optionally substituted with CrCi2 alkyl, or (^ / ^ alkoxy, R9 and R1G are each CrC18 alkyl, especially c4-c12 alkyl, which may be interrupted by one or two oxygen atoms, And X, X2, T, X and y are as defined above. In this embodiment, the comonomer τ may optionally exist, which is preferably selected from the group consisting of

30 2004 223 77

// ^ ά, where R6 is Η, or CrC8 alkyl, R8 is CVC18 alkyl, R9 and R1G are each C, C18 alkyl, especially C4-C12 alkyl, which can be one or two The oxygen atom is discontinuous, or R9 and R1G form a five- or six-membered carbocyclic ring, which can be optionally substituted with Ci_C8 alkyl group. In the first aspect of the present invention, the polymer is particularly good, and includes repeating unit 10 of the following chemical formula

(lb), and comonomers = a wide range, especially from 0 to. 6々 round, especially 0.6 to 0.4, where the sum of X and y is J R1 is the base of the following chemical formula, 31 200422377

R2 is H, 5 X1 and X2 are each independently a base of the following chemical formula

And R1G are each independently (VCm alkyl, especially c4_c12 alkyl, which can be interrupted by 10 or two oxygen atoms, and R6 and R7 are each independently H, CrC12 alkyl, cyclohexyl, c6_c24 aryl, especially benzene , Naphthyl, or biphenyl, which may be substituted with -0_Ci_Ci2 alkyl, or Ci_Ci8 alkoxy. In a second aspect, the present invention relates to polymers comprising repeating 15 units of the following chemical formula 32 2004223 77

(II), wherein R3, R4 and R5 are each an organic substituent, especially a C2-C3 () aryl group or a C2-C26 heteroaryl group, which can be optionally substituted, and X3 is a divalent bond Group, in which the repeating unit of the following chemical formula

(lib) is better, and the repeating unit of the following chemical formula

Department is particularly good. (He),

An example of a suitable divalent bonding group X3 is

33 10 2004 223 77 R71

R3; R4 and R5 are as defined above; R56 and R57 are each independently H; CrC18 alkyl; CrC18 alkyl substituted with E and / or interrupted by D5; C5-C12 Cycloalkyl, C5-C12 cycloalkyl substituted with E, C6-C24 aryl; C6-C24 aryl substituted with E; C2-C2. Heteroaryl; C2-C2 substituted with E. Heteroaryl; C2-C18 alkenyl; C2-C18 alkynyl; cvc18 alkoxy; substituted with E and / or interrupted by D (^-(: 18 alkoxy; or C7-C25 aralkyl; 10 R58) H; CrC18 alkyl; CrC18 alkyl substituted with E and / or D interrupted; C6-C24 aryl; or C7-C25 # alkyl; R59 is H; C "C18 alkyl; substituted with E and / or ≪ ^-(: 18 alkyl; C6-C24 aryl; D substituted with E; C6-C24 aryl substituted with E; C2-C2. Heteroaryl; C2-C2 () heteroaryl substituted with E C2-C18 alkenyl; C2-C18 alkynyl; (^ _0: 18 alk 15 oxy; CrC18 alkoxy substituted with E and / or D interrupted; or C7-C25 aralkyl; R71 is H, CVC18 alkyl, -ON, -CONR25R26 or -COOR27, D system -CO-; -COO_; -OCOO ·; -S-; -SO ·; -SOr; -NR25-; -SiR30R31-; -POR32 ·;- CR23 = CR24-; or -CC-; and 20 E series -OR29; -SR29; -NR25R26; -COR28; -COOR27; -CONR25R26; -CN; -OCOOR27; or halogen; of which 34 2004223 77 R23; R24; R25 And R26 are each H; c6-c18 aryl; cvc18 aryl substituted with cvc18 ^; Ci_Ci8 alkoxy; crCi8 alkyl; or cvcu alkyl interrupted by -0; or

5 υ, or 〇, R27 and R28 are each H independently; C6_C18 aryl; c6_ci8 aryl substituted with CrCi8 alkyl, or CV C, 8 alkoxy; Ci_Ci8 alkyl; or _〇_ intermittent Ci_C18 And R29 is H; C6_C1S aryl; 10 C6-C18 aryl substituted with Cl-ci8 alkyl, CrCi8 alkoxy; CrC18 ^; or crci8 alkyl interrupted by -0-, R30 and R31 each other Some are Cl-C18 alkyl, c6-c18 aryl, or c6-c18 aryl substituted with crc18 alkyl, and · R32 is crc18 alkyl, c6-c18 aryl, or c6- substituted with CrC18 alkyl C18 aryl. 15 In the second aspect of the present invention, a polymer comprising a repeating unit of the chemical formula nb (particularly a repeating unit of the chemical formula Ila, or lie) is preferred, of which,

X3 is a group of formula, wherein the dotted line represents a bond to the pyrimidine 35 2004223 77 ring, and R71 is H, alkyl, -CeN, or -COOR27, wherein R27 is H, or alkyl, which is optionally It can be interrupted by one or two oxygen atoms, especially C4-C12 alkyl, which can optionally be interrupted by one or two oxygen atoms. R3, R4 and R5 can in principle be any organic substituents, as long as it does not have a negative effect on the (electro) luminescence properties of the poly5 complex, especially H, CVC18 alkyl, substituted with E and / or interrupted by D CVC18 alkyl, C2-C18 alkenyl, C2-C18 alkynyl, CrC18 alkoxy, substituted with E and / or interrupted by D (^ -0: 18 alkoxy, C7-C25 * alkyl,

& χ5 ,. 6-. 24 Fang

Or C2-C2 () heteroaryl, the selectivity of which may be substituted, especially the group of the following chemical formula 10

36 2004 223 77

Among them, ml, m2, m3, m4, m5, m6 and m7 are integers from 1 to 10, especially from 1 to 3, X6 is H, CrC18 alkyl, CrC18 alkoxy, substituted with E and / or interrupted by D CVC18 alkyl, C6-C24 aryl, which can be optionally substituted, especially

C2-C2Q heteroaryl, 37 200422377

Can optionally be replaced,

C18 alkynyl, crcl8 alkoxy, CVCm alkoxy substituted with E and / or D interrupted, or crC25 aralkyl, X4 CVC18 alkyl, CVCm alkyl substituted with E and / or D interrupted, 5 C6-C24 aryl or C2-C2. Heteroaryl, which may be optionally substituted. X5 is CVC18 alkyl, C6-C24 aryl, or C2-C2g heteroaryl, which may be optionally substituted with -0CVC18 alkyl or -oc6-c24 aryl. R61, R62 and R63 are each H, CVC! 8 alkyl, CrC18 alkyl substituted with E and / or D interrupted, C6-C24 square, Q-C24 square substituted with E, 10 C2-C18 alkenyl, C2-C18 alkynyl, Ci -C18 alkyloxy, Ci_C18 alkyloxy substituted with E and / or D interrupted, or CrQ5 aromatic alkyl, R64 and R65 are each H, CVC18 alkyl, substituted with E and / or D interrupted CrC18 Alkyl, C6-C24 aryl, C6-C24 aryl substituted with E, C2-C20 heteroaryl, or C2-C2G heteroaryl substituted with E, and 15 D, E, R56, R57, R58 Ruler 59 and r6G are as defined above. Preferably, R56 and R57 are each H, CrC18 alkyl, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, second butyl, third butyl, 2-methylbutyl, n-fluorenyl, isofluorenyl, n-hexyl, 2-ethylhexyl, and n-heptyl, substituted with E and / or interrupted by D (VC18 alkyl, such as _ch2CH3, 20 -CH2OCH2CH3, -CH2OCH2CH2OCH3, 38 2004223 77 and -CH2OCH2CH2OCH2CH3, crCi2 cycloalkyl, such as cyclohexyl c6-c24 aryl, such as phenyl, naphthyl, and biphenyl, or c substituted with E " c Aryl, such as < 6Η4Ο (: Η3,-<: 6Η4 (χ: Η2 ™ 3, _0: 6ϋ3 ((ΧΉ3) 2 -C6H3 (OCH2CH3) 2? -c6h4ch35 -C6H3 (CH3) 25 .c6h2 (ch3) 3? 5 and -C6H4tBu OR are preferably H, CrCi8 alkyl, such as methyl, ethyl, n-propyl, isopropyl-n-butyl, isobutyl, second butyl, third Butyl, 2-methylbutyl, n-pentyl isopentyl, n-hexyl, 2-ethylhexyl, and n-heptyl, or Q_C24 aryl, such as phenyl, naphthyl, and biphenyl. Lu 10 Preferably, R59 and R6G are each H, CVC18 alkyl, such as , N-butyl, first butyl, hexyl, octyl, and 2-ethyl-hexyl, crCls alkyl substituted with E and / or D-interrupted, such as _CH2 (〇CH2CH2) wOCH3, w = l, 2, 3, or 4, C0_C24 aryl groups, such as phenyl, naphthyl, and biphenyl, C6-C24 aryl groups substituted with e, such as -C6H4ocH3, C6H4och2ch3, 15 -C6H3 (OCH3) 2? -C6H3 (OCH2CH3) 25 -C6H4CH3? -C6H3 (CH3) 25 -C6H2 (CH3) 3, and _C6H4tBu, or r59 and r6G together form a 4 to 8 member ring, preferably 5 or 5 6-membered ring, such as cyclohexyl and cyclopentyl. Preferably, R64 and R65 are each H, CVC18 alkyl, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, Isobutyl, and second butyl, or 20 C0-C24 aryl, such as phenyl, naphthyl, and biphenyl. X4 is preferably Crc18 alkyl, such as methyl, ethyl, n-propyl , Isopropyl, n-butyl, isobutyl, second butyl, third butyl, hexyl, octyl, and 2-ethyl-hexyl, or Ce-C24 aryl, such as phenyl, naphthyl , And biphenyl. X is preferably a crc18 group, such as methyl, ethyl, n-propyl, Isopropyl, 39 200422377 n-butyl, isobutyl, second butyl, third butyl, hexyl, octyl, and 2-ethyl-hexyl, C ^ C: 24 aryl, such as phenyl, Naphthyl, and biphenyl, or 〇6 < 24 aryl substituted with OR29, wherein r29 is H, crC18 alkyl, such as methyl, and ethyl, or CO_c24 aryl, such as phenyl. 5 D is preferably -CO-; -COO-; -OCOO-; each; -so-; -sor;-NR25-; and E is preferably _〇R29; _SR29; -NR25R26 bu Co〇R28; "COOR27;_CONR25R26; or --CN; where R25; R27; R28 and R29 are each independently H; CrC18 alkyl; such as, methyl; ethyl; n-propyl; isopropyl; n-butyl; isobutyl; Second butyl; hexyl; octyl; and 2-ethyl-hexyl; C6-C24 10 aryl; such as, phenyl; naphthyl; and biphenyl. Preferably, at least one of R1, R2 and R3 is a C6-C24 aryl group or a C2-C20 heteroaryl group, which may be optionally substituted. In this regard, it includes the chemical formula Ila (wherein R4 is fluorene, and R3 and R5 are each independently a C6-C24 aryl group, or a C2-C20 heteroaryl group), or Iic (wherein, R3 is fluorene, and R4 and R5 are each other Polymers which are individually repeating units of C6-15 C24 aryl or C2-C2Q heteroaryl) relative to each other having the formula IIb (wherein R3, R4, and R5 are each C6-C24 aryl or C2-C2 hetero Aryl, in which the c6-C24a aryl or C2-C20 heteroaryl can be optionally substituted) repeating units of these polymers are preferred.

40 2004223 77 where 'R59 and r60 are each Ci_Ci8 alkyl group, especially C4_Ci2 alkyl group, which can be interrupted by one or two oxygen atoms, among which is a repeating unit polymer containing the chemical formula lib, where R3, R4 , And R5 are independent of each other

And polymers containing repeating units of formula (Ila),

And a polymer containing a repeating unit of chemical formula (lie), wherein R3 is η,

Department is particularly good. The polyfluorene of the present invention comprises repeating units of chemical formula II in an amount of 0.5% to 5% (especially 41 2004 223 77 is 40 mol% to 60 mol%), wherein all of the repeating units (monomers) The sum is 100 mol%. Therefore, in addition to the repeating unit of Chemical Formula II, the polymer of the present invention may further include a total of 5 monomers of Chemical Formula II in an amount of up to 99.5 mol% (especially in an amount of 60 mol% to 40 mol%). The appropriate co-single system is selected from the group consisting of

42 2004 223 77

43 2004 223 77

Among them, P is an integer from 1 to 10, particularly 1,2 or 3, q is an integer from 1 to 10, especially 1,2 or 3, 5 s is an integer from 1 to 10, and particularly 1,2 or 3 ,

R72 is H; CVCu aryl group; CfCig square group substituted with CrCls alkyl or CrCi8 alkoxy group, alkyl group; Ci_ci8 alkyl group with _〇_ interruption · R56, R57, R58, R59, R6G, R64 and R65 series As defined above, or R59 and R60 together form a group of chemical formula = CR100R101, where 10 R1GG and R1G1 are each H, CrCls alkyl groups, substituted with E and / or D interrupted CrCls alkyl groups, CVC24 aryl groups, and E-substituted c6-C24 aryl, or CVC2. Heteroaryl, or C2-C2G heteroaryl substituted with E, wherein D and E are as defined above.

Preferably, R56 and R57 are each H, CrC18 alkyl, such as 15 methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, second butyl, or third butyl. , 2-fluorenylbutyl, n-pentyl, isopentyl, n-hexyl, 2-ethylhexyl, and n-heptyl, CrC18 alkyl substituted with E and / or D interrupted, such as -CH2OCH3,- ch2och2ch3, -ch2och2ch2och3, and -ch2och2ch2och2ch3, c5-c12 cycloalkyl, such as cyclohexyl, 20 C6-C24 aryl, such as phenyl, naphthyl, and biphenyl, or c6-c24 aromatic substituted with E Groups, such as -C6H4OCH3, -C6H4OCH2CH3, -C6H3 (OCH3) 2, -c6h3 (och2ch3) 2, -c6h4ch3, -c6h3 (ch3) 2, -c6h2 (ch3) 3, 44 200422377 and -C6H4tBu OR58 H, crcls alkyl, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, second butyl, third butyl, 2-methylbutyl, n-pentyl Group, isopentyl, n-hexyl, 2-ethylhexyl, and n-heptyl, or c6-C24 aryl, such as phenyl, naphthyl, and biphenyl. If R59 and R6 ° form a base of chemical formula = CR1G ° R1G1, τ is more preferably the base of the following chemical formula

Among them, R102 and R103 are each a CrCi8 alkyl group, a CrCi8 alkoxy group, a 10 C6_Cl0 aryl group, a C6-Cio aryloxy group, or a bis (C "C18 alkyl) amino group. Among them, the aryl group or the aryloxy group may be Selectively substituted by Cl_C8 alkyl (1 ^-: 6- 6,512, 〇83) 〇 Preferably, R59 and R6. Each of them is H, Ci_Ci8 alkyl, such as n-butyl, second butyl, hexyl, Octyl, and 2-ethyl-hexyl, substituted with E and / or C1-C18 alkyl group interrupted by 150, such as -CH2 (OCH2CH2) wOCH3, W = 1, 2, 3, or 4, C ^ C24 aryl, such as phenyl, naphthyl, and biphenyl, C24 aryl substituted with E, such as -C6H4OCH3, _C6H4OCH2CH3, " c6H3 (〇ch3) 25 -c6h3 (〇ch2ch3) 2? -c6h4ch35 -c6h3 (ch3) 25 -C6H2 (CH3) 3, and -C6H4tBu, or R59 and R6G together form a ring of 4 to 8 members, 20 is preferably a ring of 5 or 6 members, such as cyclohexyl, Preferably, R64 and R65 are each H, CrC18 alkyl, such as methyl 45 2004223 77, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, and thionyl. Dibutyl, or c6-c24 aryl, such as phenyl, naphthyl, and biphenyl. The examples relate to a polymer 5 including a repeating unit of the chemical formula lib (especially a repeating unit of the chemical formula Ila or lie) and a comonomer y, wherein X is in the range of 0.005 to 1, especially 0.4 to 0.6, and y It ranges from 0.995 to 0, especially from 0.6 to 0.4. Among them, the sum of X and y is 1. Among them, X3 is the base of the following chemical formula.

10 Among them, the dotted line represents the bond to the pyrimidine ring, and R3, R4, and R5 are each independently a base of the following chemical formula

T is the base of the following chemical formula

, Especially 200422377

Among them, s is 1, or 2, R56, R57, and X6 are each independently CrC18 alkyl, substituted with 5 E and / or D-interrupted CrC18 alkyl, C6-C24 aryl, and C6-C24 aromatic substituted with E base,

R59 and R6G are each CrC18 alkyl, each substituted with _〇r29 and / or with -0- interrupted CrC18 alkyl, R71 is H, -CONR25R25 or -CN, of which 10 D is -〇-, or -NR25 -, E is -OR29, -SR29, or -NR25r25, wherein R25 is H, CrC18 alkyl, or C6_c24 aryl, and R29 is CrC18 alkyl, C6-C24 aryl. A particularly good implementation is about the repeating unit containing the chemical formula 47 2004223 77 (including the repeating unit of the chemical formula IIa, or the repeating unit of the IIc) and the co-relying polymer 'wherein' 1 ranges from 0.5 to i, especially And y is in the range of 0.995 to 0, especially 0 to 6 in which X and the sum are 1,

Bond, and R71 is H, alkynyl, < ξN, or _c〇〇〇27, wherein, is Η or C "C18 alkyl, which can optionally-or two oxygen atoms are interrupted, especially ': CrCu Alkyl, which may be interrupted by one or two oxygen atoms, 10 1 T is a radical of the formula R3, R4 and R5 each independently H,

Among them, R59 and R60 are each a CrCi8 alkyl group, especially a C4_Cq alkyl group 48 2004 223 77 group, which can be interrupted by an oxygen atom.

or

Is preferred; and a polymerization unit comprising a repeating unit of the following chemical formula X3-

(lib), 5 of which R3, R4, and R5 are independent of each other

Or and polymers containing repeating units of the formula

(Ila), wherein R4 is Η, and R3 and R5 are each 49 422377

And polymers containing repeating units of the following formula

Represents a bond to a pyrimidine ring, and r "is H, alkyl, _CeN, or -COOR27, wherein R27 is η; or Ci_Ci8 alkyl; it may be optionally interrupted by 10 one or two oxygen atoms, particularly Is a C4-C12 alkyl group, which may be interrupted by one or two oxygen atoms, and T is a group of the formula 50 2004223 77

Among them, R59 and ROG are each CrC18 alkyl group, especially C4-C12 alkyl group, which can be interrupted by one or two oxygen atoms.

Department is particularly good. 5 The term "polymer" according to the present invention includes oligomers having a weight average molecular weight of < 3,000 Daltons, and polymers having a weight average molecular weight of 3,000 Daltons or more. The polymer of the present invention preferably has a weight average molecular weight of 50,000 Daltons or more, more preferably 100,000 Daltons or more, and most preferably 10 150,000 Daltons or more; more preferably 1, 000,000 Daltons or less, more

The preferred range is 500,000 Daltons or less, and the preferred range is 250,000 Daltons or less. The molecular weight is determined by gel permeation chromatography using polystyrene standards. Further embodiments of the present invention are represented by monomers of the following chemical formula 15

(III), special department 51 2004 223 77

(mb); and / or

(IV), special department

X11

(IVb), or (IVc); wherein R1, R2, R3, R4, and R5 are each an organic substituent, especially c〆 such as aryl or 0: 2 ·. Heteroaryl, which can be optionally substituted, X1, X2, and X3 are each a divalent bonding group and X11 is a _ prime atom in each case, or 氺 (0Η) 2, _Β (〇γ1) 2 or-Β [〇 > 2 crc1Q alkyl, and Y2 is -CY3Y4-CY5Y6-, or-〇, where γ1 in each case is individually in each case individually crc1G alkyl, such as, 52 10 200422377 cW-CYf-CYuY12, among which γ3, γ4, γ5, γ6, γ7, γ8, γ9, υ10, r and υ12 are each hydrogen or CrCi. Burning group, especially -c (ch3) 2c (ch3) 2, or _C (CH3) 2CH2C (CH3) 2, which is the starting material for the manufacture of polymers of chemical formulas I and II, but with the condition of 2_benzene Base_4,6_ 5 bis (p-mophenyl) «(A.L. Vais et al., Izv Slot otd Akad Nauk · SSSR, Vol. 6, 1975, 144] 46) and 2,4,6 three (pair Mophenyl)% ^ (M. Bajic et al., Molecules (Kancai's Book 6, No. 5, 2 deleted, 477_480) are excluded. The starting compounds are known, or can be based on known procedures or It is made by similar persons. The hydrazone compound of the present invention is, for example, a derivative of a known benzophenone compound: US_A_3,442,898, US_A_5,597,854 and still-in-5,753,729, the relevant parts of which are here It is incorporated by reference. The specific compounds of the present invention can be prepared, for example, according to the following procedures or the like: 15

x2-x11

Where 'R1, R2, X1, and χ2 are as defined above' and "systems of the halogen atom 0 > ammonium hydrogen chloride are added to the 2-propanol in crc4 alcohols (e.g., methanol, ethanol, propanol or butanol) Dilute ketones. Tests (for example, test metal nitrogen oxides or oxo 20 oxides, such as sodium methoxide or potassium hydroxide) are added and the solution is mixed in the presence of as fine as dry working gas (see, For example, Example 8) of European Patent Application No. 03405044.07.6. 53 2004223 77 The boron-containing compound of the chemical formula (ιν) can be produced by any suitable method. One of the reaction conditions for producing a boron-containing compound Examples are described in Macromolecular Rapid Communications by Remmers et al., Volume 17, 239-253 (1996). Compounds of formula (IV) 5 (which are substituted with chlorine or bromine di) are prepared by Two equivalents of butyllithium are converted into the corresponding dilithium derivative. The dilithium derivative reacts with the trialkylborate and the subsequent hydrolysis reaction to produce the diboronic acid derivative. The diboronic acid derivative and the alkylene glycol (Such as ethylene glycol) Bis (cyclic) borate derivatives. 10 Halogen-based gas, chlorine, & odor and crack. Crc18 alkyl-based branched or unbranched groups such as methyl, ethyl, propyl, isopropyl, N-butyl, second butyl, isobutyl, third butyl, 2-ethylbutyl, n-pentyl, isopentyl, 1-methylpentyl, 1,3-dimethylbutyl, N-hexyl, 1-methylhexyl, n-heptyl, isoheptyl, 1,1,3,3-tetramethylbutyl, 1-methylheptyl, 3-methyl 15 heptyl, n-octyl, 2-ethylhexyl, 1,1,3-trimethylhexyl, 1,1,3,3-tetramethylpentyl, nonyl, decyl, undecyl, 1-methylundecyl , Dodecyl, 1,1,3,3,5,5-hexamethylhexyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptyl, or ten Octyl. ≪ ^-(: 18 alkoxy is a linear or branched alkoxy group, for example, methoxy, 20 ethoxy, n-propoxy, isopropoxy, n-butoxy , Second butoxy, third butoxy, pentoxy, isopentyloxy or third pentoxy, heptyloxy, octyloxy, isooctyloxy, nonyloxy, decoxy, ten One Oxy, dodecyloxy, tetradecyloxy, pentadecyloxy, hexadecyloxy, heptadecyloxy, and octadecyloxy. 54 2004223 77 C2-Cls alkenyl straight chain Or branched alkenyl, such as propyl, methylpropenyl, isopropenyl, 2-butenyl, 3-oxenyl, n-pent-2,4-monomethyl, 3-methylbut-2 -Alkenyl, n-dodec-2-enyl, isododecenyl, n-dodecenyl. Vinyl, allenyl, isobut-n-oct-2-enyl, alkenyl or n- Eighteen-4- 10 15 c2.24 alkynyl branched chain mosquitoization, Lujia is C28 alkynyl, can be unsubstituted or substituted, such as, ethynyl, Mum # 4-yl, 1.pentyne _5 · group, 2 · methyl_3_buta_2_yl group, glutarate_3_ group, U-pentadi · 5 group, i-hexyne groups, cis_3_methyl group Pentenyl- [group, trans-3-methyl-2-pentenyl small group, u · hexamethylene_5_ group, i octyne groups, i-nonyne_9_ group, l decyl fast · 10-based or i twenty-four fast a-based. The C4-C18 cycloalkyl group is preferably a C5-C12 cycloalkyl group, such as cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, and cyclododecyl. Cyclohexyl and bad fluorenyl are the best.

20 cvc ^ alkenyl ', for example, vinyl, allyl, butenyl, pentyl, hexyl, heptyl or octyl. The aryl group is generally a C6-C3Q aryl group, preferably ρ ρ »M3〇π soil will soon hold you, -C24 aryl group, which can be optionally substituted, such as phenyl, 4-methylphenyl, 4-methoxyphenyl, phenyl, biphenyl, 2-fluorenyl, phenanthrene, alfalfa A is not fluorenyl, tetmcyl, pentacyl, hexacyl, biphenyl Triphenyl or bitetraphenyl. The alkyl group is preferably a C7-C15 aromatic alkyl group, which may be substituted, such as,

Benzyl, 2-benzyl-2-propyl, cold-phenethyl, α, α-dimethylbenzyl, phenyl-butyl, ω-phenyl-octyl, phenyl-deca Dialkyl or 3- 55 2004 223 77 methyl-5- (1 ', 1', 3 ', 3'-tetramethyl-butyl) -benzyl. A C2-C26 heteroaryl system has a ring or condensed ring system of five to seven ring atoms with nitrogen, oxygen, or sulfur systems as possible heteroatoms, and typically has at least six conjugated 7Γ-electrons with 5 to 30-atom unsaturated heterocyclic group, 5 such as thienyl, benzo [b] thienyl, dibenzo [b, d] thienyl, thienyl, pyranyl, glycosyl, 2H -Ranyl, benzopyranyl, isobenzopyranyl, dibenzocrotyl, phenoxy 13 ceryl, α-biroyl, imidino, and. ratio. Sitting on the base. Than ° fixed base, second fixed base, triple base, fixed base, base base, ΰBiluo base, 12 lead mouth σ Qin, different, mouth base, deep base, 11 lead sialyl, purine base, 10 17 Kuihe Base, shout 11 rueki, isoσ ϋ ϋ rueki, 酜 基 基 基, naphthalene 17 基 基, 嗤 σ 嗤 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 [ , Benzotriazolyl, benzoxazolyl, phenanthridyl, acridineyl, white pyridyl, phenanthroline, phenazinyl, isothiazolyl, phenothiazyl, isoxazolyl, furoxyl, or Oxazosinyl, which may be unsubstituted or substituted. 15 Individual examples of five- or six-membered rings formed by R6 and R7 and R56 and R57 are heterocycloalkanes or heterocycloolefins having 3 to 5 carbon atoms, which may have an additional selected from nitrogen, oxygen and Heteroatoms of sulfur, for example,

56 Possible substituents of the above groups (^ _ (: 8 alkyl, hydroxy, thiol, Cr 8 alkyl, thio, halo, halo), radical, carbyl, keto, Fluorenyl, ester, carbamoyl, amine, nitro or silyl. The term "haloalkyl" means a group that is partially or fully substituted with a halogen such as trifluoro, such as trifluoro Methyl, etc. "" Acid, keto, ester, carbamoyl, and amine groups include those substituted with alkyl, cycloalkyl, aryl, aralkyl, or heterocyclic groups, of which alkyl, Cycloalkyl, aryl, aralkyl, and heterocyclic groups may be unsubstituted or substituted. The term, silyl, means a group of the formula -SiRl05R106R107, wherein R105, R106, and R107 are each independently An alkyl group, especially a Ci_C4 alkyl group, a c6_C24 aryl group, or a C7_Ci2 aralkyl group such as a trimethyllithium group. If a substituent (such as R6, R7, R56, and R57) occurs more than once in the chemical formula, it It may be different in each case. As mentioned above, the aforementioned radicals may be replaced by E and / or (if desired) interrupted by D. Of course, the interruption This is only possible when there are at least 2 carbon atom radicals connected to each other by a single bond; the Q-Cu aryl group is not interrupted; the interrupted arylalkyl or alkylaryl contains unit D based on the alkyl moiety. CrCi8 alkyl systems with one or more E substituted and / or one or more D discontinuities, for example, (CH2CH2〇) n-Rx, where η is a value in the range of 1-9, and R is Η or CrCw Base or C2-C1 () roasting group (for example, co-CH (C2H5) C4H9), CH2-CH (0Ry,)-CH2_0-Ry, wherein Ry is Ci_Ci8 alkyl, C5-C12i alkyl , Phenyl, C7-C15 phenyl alkyl, and Ry, containing the same meaning as Ry or H; 200422377

CrC8 alkylene-COO-RZ, for example, ch2coorz, ch (ch3) coorz, C (CH3) 2COORz, where Rz is H, CVC18 alkyl, 9-Rx, and Rx includes the definitions of the above households; ch2ch2 -o-co-ch = ch2; ch2ch (oh) ch2-o-co- 5 C (CH3) = CH2. The polymer containing the bases of the formulae (I) and (π) may be produced by any appropriate method, but is preferably produced by a method described below. The condensation reaction of aromatic borate and bromide (commonly referred to as the "Suzuki reaction") is tolerant of the existence of various organic functional groups, and is composed of N. Miyaua and A. Suzuki in Chemical 10 Reviews, Volume 95, 457-2483 (1995). This reaction can be applied to make high molecular weight polymers and copolymers. In order to manufacture a polymer corresponding to Chemical Formula I or II, a dibromide corresponding to Chemical Formula III or IV or a mixture thereof and an equivalent weight corresponding to a diboronic acid or a diborate or a mixture thereof corresponding to Chemical Formula III or IV, preferably It is a total of 15 monomers, which react under the catalysis of Pd and triphenylphosphine χ14χχ11 # j where X11 is a _ prime atom in each case, or -B (〇Η) 2, ^ (ΟΥ% or -BC ° > 2 where Y1 is a cvc10 alkyl group in each case and Y2 is a C2-C1G alkylene group in each case, such as —CY3Y4-CY5Y6 ·, or — 20 CY7Y8-CY9Y10- CYUY12 -, In which Υ3, Υ4, Υ5, γ6, γ7, Υ8, γ9, γιο Υ11 and Υ12 are each independently hydrogen, or crc1G alkyl, especially -C (CH3) 2C (CH3) 2_, or -C (CH3 ) 2CH2C (CH3) 2-. The reaction is typically carried out at about 70 ° C to 120 ° C and 58 200422377 in an aromatic hydrocarbon solvent (such as toluene). Other solvents such as dimethylformamide and tetrahydrofuran It can also be used alone or mixed with aromatic hydrocarbons. Aqueous bases (preferably sodium rhenium or sodium bicarbonate) can be used as HBr scavengers. Depending on the reactant Depending on the reactivity, the polymerization reaction can take 2 to 100 hours. Organic bases (such as 5 tetrakisyl-based rat emulsions) and phase transfer catalysts (such as TBAA) can promote the activity of the shed (see, for example, Leadbeater &Marco; Angew · Chem. Int. Ed "2003, 42, 1407 and references cited therein). Other changing reaction conditions are shown in the journals of organic chemistry of T. I. Wallow and B. M. Novak, Volume 59, pages 5034-5037 (1994); and M. Remmers, M. Schulze, and G. Wegner, 10 Macromolecular Rapid Communications, Volume 17, pages 239-252 (1996) The alternating copolymer is formed when the dibromo χ11-(-τ + χ11 compound corresponding to chemical formula (III) or (IV) is reacted with the diborate corresponding to chemical formula y, -bc ° v 15 where, X11 is individually -B (ΟΗ) 2, -Βργ% * 0 in each case, where Υ1 is individually a CrC1G alkyl group in each case, and 112 is a CVG individually in each case. Alkyl groups such as- CY3Y4-CY5Y6-, or -CY7Y8_CY9Y10- CYUY12-, where Y3, Y4, Y5, Y6, Y7, Y8, Y9, Y10, Y11 and Y12 are each independently hydrogen, or Ci-C1G alkyl, particularly 20-C (CH3) 2C (CH3) 2-, or _C (CH3) 2CH2C (CH3) 2-. If desired, monofunctional aryl halides or aryl chelates can be used as chain terminators in these reactions, which can cause the formation of terminal aryl groups. 59 Polymerization methods involving only dibasic tube-like reactants can be performed using nickel coupling reactions. One such coupling reaction is described in Colon et al.'S Journal of Polymer Science, Part A, Polymer Chemistry Edition, Vol. 28, p. 367 (1990), and Colon et al. Journal of Organic Chemistry

Chemistry), Book 51, Page 2627 (1980). The reaction is typically in a polar aprotic solvent (eg, dimethylacetamide) with a catalytic amount of nickel salt, a large amount of triphenylphosphine, and extremes. Excessive dust is carried out. A variant of this method is described by Ioyda et al. In the Bulletin of the Japanese Chemical Society, Vol. 63, p. 80 (1990), in which organic soluble iodide is used as an accelerator. Another nickel coupling reaction is disclosed by Yamamoto in Polymer Science Development, Book π, Page 1153 (1992), where the mixture of dihalo aromatic compounds is an excess of nickel (1, 5 in an inert solvent) • Cyclooctadiene) complex treatment. When applied to a reactant mixture of two or more aromatic dihalides, all nickel-containing reactions produce a substantially random copolymer. These polymerization reactions can be terminated by adding a small amount of water to the polymerization reaction mixture, which replaces the terminal group with a hydrogen group. In addition, monofunctional aryl functional compounds are used as chain terminators for these reactions, which can cause the formation of terminal aryl groups. In the examples, the polymers of the present invention contain conjugated groups other than the pyrimidinyl groups described above. "Conjugating group" means a moiety containing a double bond, a triple bond and / or an aromatic ring. Examples of such groups are the above-mentioned co-monomers. Incorporation of the base into the polymer can be used to improve the absorption, ionization potential, and / or electronic properties of the polymer. These polymers can be made by the methods described above and include at least ―common compounds different from the compounds described above. These compounds (hereinafter referred to as, comonomers, etc.) have a functional group capable of copolymerizing them with a pyrimidine compound. For example, a di-functional co-monomer is preferably used in the coupling reaction of nickel coupling with a bidentate-functional pyrimidine compound; a di-I-functional co-monomer is preferably used with a pyrimidine-diboronic acid or a pyrimidine _ Diborate conjugate is used for 5 purposes, and the conjugated comonomer loaded with diboric acid or diborate is preferably used in conjunction with a dihalo mouth conjugate. In order to make the polymer of the present invention, more than one diboric acid / diborate and more than one dibromide can be used in the Suzuki polymerization reaction, so long as the total mole of diboric acid / diborate is substantially equal to the total dibromide the amount. 10 Nickel coupling polymerization produces a substantially random copolymer containing units containing pyrimidinyl groups and units derived from other comonomers, while Suzuki polymerization produces alternating copolymers. The sequence of the monomer units forming the copolymer can be controlled by controlling the order and composition of the monomer feed of the Suzuki reaction. For example, high molecular weight copolymers that mainly contain large pyrimidine homopolymer blocks connecting 15 to short alternating pyrimidine comonomer oligomer blocks can be prepared by first incorporating the reactants in the appropriate proportions in the reaction Alternate pyrimidine comonomer oligomers are obtained and then incorporated into the remaining mock monomers, which have a complete balance of shed acid groups and desert groups. Generally, the polymer of the present invention includes a terminal moiety & wherein El is a 20 hydrogen or aryl moiety, which can be optionally substituted with a reactive group capable of chain extension or cross-linking, or tri (cvcy) Alkylsiloxy. When used herein, a reactive group capable of chain extension or cross-linking refers to any group that can react with another identical group or another group to form a link for the manufacture of an oligomer or polymer. Preferably, the reactive group is fused to the aromatic soil of Eila, glycidol 61 2004223 77 test, acrylic acid purpose, methacrylic acid purpose, vinyl, ethynyl, maleimide, resistant Nadimide, trifluorovinyl ether moiety or cyclobutene moiety.

The polymer of the present invention (wherein E1 is a reactive group as defined above) 5 can be crosslinked to form a solvent-resistant heat-resistant film at 100 ° C or more (more preferably 15 (TC or more)). Preferably, these cross-linking reactions occur at 350 ° C or less (more preferably 300 ° C or less, and most preferably 250 ° C or less). The crosslinkable polymerization of the present invention It is stable at 100 ° C or more and preferably at 150 ° C or more. "Stable" when used herein means that these polymers are not crosslinked at the stated temperature or below 10 Action or polymerization reaction. If the crosslinkable material is desired, E1 is preferably vinylphenyl, ethynylphenyl, or 4- (or 3-) benzocyclobutylfluorenyl. In another embodiment ' E is selected from the group of the aldehyde derivative of the chemical formula -C6H4-O-Y, wherein Y is

_J 15 H2 «. If desired, the crosslinkable group may be present elsewhere in the polymer chain. For example, one substituent of the comonomer T may be a crosslinkable group E1. The end-capping agent E ^ × ^ 1 is as defined above, and X is C1 or Br) is formed in the polymer formed under the condition that the end is blocked by the reactive group E1 and is included in the polymer of the present invention. The reactions which can be used for this purpose are the nickel coupling reaction and the Suzuki reaction as described above. The average degree of polymerization is controlled by the molar ratio of monomer to capping agent. 62 200422377 Depending on the method of manufacture 'The polymer of the present invention may be a homopolymer, a block copolymer, a random copolymer, or an alternating copolymer. Another aspect of the invention relates to polymer blends containing from 1 to 99% of at least one pyrimidine-containing polymer of the invention. The remaining 51 to 99% of the blend consists of one or more polymeric materials selected from bond-growth polymers such as polystyrene, polybutadiene, poly (methyl methacrylate) And poly (ethylene oxide); stage-growth polymers such as phenoxy resins, polycarbonates, polyamides, polyesters, polyurethanes, and polyimines; and cross-linked polymers such as , Cross-linked epoxy resin, cross-linked phenol resin, cross-linked 10 acrylate resin and cross-linked urethane resin. Examples of these polymers can be found in polymer chemical manufacturing methods (preparative methods of poiymer)

Chemistry), W · R · Sorenson and Τ · W_ Campbell, 2nd edition,

Interscience publishers (1968). Conjugated polymers can also be used in blends, such as poly (phenylene vinylene), substituted 15 poly (phenylene vinylene), substituted polyphenylene, and polythiophene. Examples of such co-light polymers are shown by Greenham and Friend in State Physics, Book 49, pp._149 (1995). The present invention, on the other hand, is a film formed from the polymer of the present invention. These films can be used for polymer light-emitting dipolarity. Preferably, these films are used as the 20 light emitting layer. These polymers can also be used as protective coatings for electronic devices and are fluorescent coatings. The thickness of the coating or film depends on the end use. Generally, this thickness may be from 0.001 to 200 microns. In the embodiment in which the coating is used as a fluorescent coating, the thickness of the coating or film is from% to · micrometer. In the embodiment in which the coating is used as an electronic protective layer, the thickness of the coating can be 5 to 20 microns. In the embodiment in which the coating is used for a polymer light emitting diode, the thickness of the formed layer is from 0.05 to 2 micrometers. The polymer of the present invention forms a good film without holes and deletions. These films can be made by means known in the art, including spin coating, spray coating, dip coating and pad coating. These coatings are made by a method comprising applying a composition to a substrate and exposing the coating composition to conditions for forming a thin film. The conditions for film formation depend on the coating technique and the reactive end groups of the aryl moiety. In a preferred embodiment, the composition applied to the substrate comprises a pyrimidine polymer dissolved in a general organic solvent. Preferably, the solution contains 10 to 10% by weight of the 10 polymer. The composition is applied to the substrate by a desired method, and the solvent is evaporated. Residual solvents can be removed by vacuum and heating. After the solvent is removed, if necessary, the coating is exposed to the conditions necessary for curing the film to produce a film having high solvent resistance and heat resistance. The film is preferably of substantially uniform thickness and has no small holes in the shell. In another embodiment, the polymer may be partially cured. 15 This is called the B-phase. Another embodiment of the present invention relates to an optical device or a component thereof comprising a substrate and a polymer according to the present invention. The device according to the present invention may be manufactured in accordance with the disclosure of WO99 / 48160, the contents of which are incorporated herein by reference. The polymer 20 according to the present invention may be present in the device as the sole luminescent polymer or as a component further comprising a blend of electron holes and / or electron transport polymers. In addition, the device may include individual layers of the polymer of the present invention, a hole-transporting polymer, and / or an electron-transporting polymer. In one embodiment, the optical device includes an electroluminescent device including 64 2004223 77 (a) a charge spray layer for spraying a positive charge carrier, (b) a charge spray layer for spraying a negative charge carrier, (c) The light-emitting layer located between the layers (a) and (b) comprises a polymer according to the invention. The (a) layer may be a positively-charged carrier transport layer located between the light-emitting layer (c) and the anode electrode layer, or may be an anode electrode layer. The (b) layer may be a negatively-charged carrier transport layer located between the light-emitting layer (c) and the cathode electrode layer, or may be a cathode electrode layer. Alternatively, the organic charge transport layer may be located between one of the light emitting layer (C) and the charge carrier ejection layers (a) and (b). 10 Electroluminescent devices emit light below 520 nm (particularly between 380 nm and 520 nm). The electroluminescence device has an NTSC coordinate between about (0.12,005) and about (〇16,00), and is especially about (14,008) 2NTSC coordinates. It is to be understood that the light-emitting layer may be formed from an exchange or mixture of one or more polymers I5 according to the present invention and optionally further polymers of different polymers. Further different polymers may be so-called electron hole transport polymers (ie, to improve the efficiency of electron hole transport to luminescent materials) or electron transport polymers (ie, to improve the efficiency of electron transport to luminescent materials). Preferably: the blend or mixture comprises at least 0.01% by weight of the polymer 20 according to the present invention, preferably 0.2 to 50% by weight, and more preferably 0.5 to 30% by weight. Organic electroluminescence devices typically consist of an organic film sandwiched between an anode and a cathode. Thus, when positive partial dust is applied to this device, electron holes are sprayed from the anode to the organic film, and electrons are sprayed from the cathode to the organic film. 1 The combination of a sub-hole and an electron can generate an exciton, which can be extended to the ground state by releasing the photon. In fact, anodes are generally mixed oxides of tin and rhenium because of their electrical conductivity and transparency. Mixed oxide (ITO) is deposited on a transparent substrate, such as glass or plastic, so that the light emitted by the organic thin film can be observed. Organic thin films can be composed of several individual layers, each of which is designed for a particular function. Because the electron hole is sprayed from the anode, the layer adjacent to the anode must have the function of transporting the electron hole. Similarly, the layer adjacent to the cathode needs to be capable of transporting electrons. In many examples, the electron hole_ (electron) transport layer also functions as a light emitting layer. In some examples, a layer can perform a combination of electron holes and electron transport and light emitting functions. The individual layers of the organic film may be polymers in nature, or a mixture of polymer films and small molecule films deposited by thermal evaporation. Preferably, the total thickness of the organic film may be about 1000 nanometers (nm). More preferably, the total thickness is less than 500 nm. Optimally, the total thickness is > at 300 nm. # Fatherly, the thickness of the active (light-emitting) layer is less than milligrams (nm). More preferably, the thickness is in the range of 40 to 160 nm. 15 glass substrates and anodes can be coated with cleansers, organic solvents, and ultraviolet and ozone. It can also be coated with a thin layer of conductive material first to promote electron hole ejection. These substances include copper phthalocyanine polyaniline and poly (3,4-ethylidene diphenoxyphene) (pedt); the latter two are by using strong organic acids (for example, poly (phenylethyl acetic acid) ) Is doped to form its conductive 20 form. Preferably, the thickness of this layer is 200 angstroms or less; more preferably, the thickness is 100 nm or less. In the case where the electron hole transport layer is used, the polymer amine described in US Patent No. 5,728,8Gm can be used. Other known electron tunneling polymers (such as polyethylene leaf casts) can also be used. The resistance of this layer 66 2004223 77 to the corrosive action of the polymer film solution to be subsequently applied is obviously important for the successful manufacture of multilayer devices. The thickness of this layer may be 500 nm or less, preferably 300 nm or less, and most preferably 15011111 or less. Where the electron transport layer is used, it can be applied by thermally evaporating the low molecular weight material or by coating the polymer with a solvent solution that does not cause significant damage to the base film. Examples of low molecular weight materials include metal complexes of

Burrows et al. In Applied Physics Letters, Vol. 64, pp. 2718-2720 (1994), ι〇-Medium benzopyrene sigmaine 10 metal complexes (eg Hamada et al. In chemical letters

Letters), pp. 906-906 (1993)), ι, 3,4-oxadiazole (as Hamada specializes in Optoelectronics-Devices and Technologies, Vol. 7, pp. 83_93 (1992 )), 1, 3, 4-triamidine (as described by Kido et al. In Chemistry Letters, 15 pp. 47-48 (1996)), and dibenzyl bicarbonate Imine (as described by Yoshida et al. In Applied Physics Letters, Vol. 69, pp. 734_736 (1996)). Polymer electron transport materials are exemplified by the following: polymers containing 1,3,4-oxadiazole (such as Li et al. In the Journal of Chemical 20 Society, 2211 · 2212 (1995), Yang And Pei in the Journal of Applied Physics, Vol. 77, pp. 4807-4809 (1995), polymers containing 1,3,4-triazoles (such as Strukelj et al. In Science (Science ), Vol. 267, pp. 1969-1972 (1995), quinoxaline-containing polymers (e.g. Yamamoto et al., Japanese Journal of Applied Physics (Japan 67

Journal of Applied Physics), Vol. 33, pages L250-L253 (1994), O'Brien et al. Synthetic Metals, Vol. 76, pages 105-108 (1996)), and cyanide Base-PPV (as described by Weaver et al. In Thin Solid Films, Vol. 273, pp. 39-47 (1996)). The thickness of this layer may be nm or less, preferably 300 nm or less, and most preferably 150 nm or less. Metal cathodes can be deposited by thermal evaporation or by sputtering. The thickness of the cathode can be from 100 nm to 10,000 nm. Preferred metals are calcium, magnesium, indium and aluminum. Alloys of these metals can also be used. Aluminum alloys containing 1 to 5% bells and magnesium alloys containing at least 80% magnesium are preferred. In a preferred embodiment, the electroluminescent device includes at least one electron hole transporting polymer film and a light-emitting polymer film, which includes the polymer of the present invention and is disposed between the anode material and the cathode material so that it is applied at the applied voltage. When the device is forward biased, electron holes are ejected from the anode material into the electron hole transport polymer film 'and electrons are ejected from the cathode material into the light emitting polymer film' causing light to be emitted from the light emitting layer. In another preferred embodiment, the electron hole transporting polymer layer is configured such that the layer near the anode has a lower oxidation potential, and the adjacent layer has an emulsification potential that is gradually higher than that of the gate. An electroluminescent device having a relatively high light output per unit of electricity can be made. The gate uses a light-emitting polymer electron hole to transport the polymer film.-When used herein, it means that when it is deposited between the two electrodes in a field and the electron hole is sprayed from the anode, it can transport 5k field to the light-emitting polymer. The polymer thin film polymer code—the triaryl radical is composed of electrons and the 200422377 film is used here to mean that its laser state can be reduced by emitting photons (preferably corresponding to the wavelength in the visible range). A polymer film layer that is slow to the ground state. The term "anode material" as used herein refers to a translucent or transparent conductive film with a work function between 4.5 electron volts (eV) and 5.5 ev. Examples are gold, 5 Silver, copper, indium, iron, zinc, tin, chromium, titanium, vanadium, cobalt, nickel, lead, manganese, tungsten, etc .; metal alloys, such as magnesium / copper, magnesium / silver, magnesium / ming, aluminum / indium, etc. Semiconductors such as Si, Ge, GaAs, etc .; metal oxides such as indium-tin-oxide ("ITO"), ZnO, etc .; metal compounds such as CuI, etc., and conductive polymers such as, Polyacetylene, polyaniline, polythiophene, poly 10 to π each, polyparaphenylene. Indium The oxides of tin and mixed oxides are preferred. The best is ITO, especially ITO on glass (as the substrate). The term "cathode material" when used herein means 2.5 eV and 4_5 ev Conductive thin film of work function. Examples are alkali metals, alkaline earth metals, Group 13 elements, silver and copper, and alloys or mixtures thereof, such as sodium, chain, potassium, about, fluoride (Uf), 15 nanometers " unalloyed, money, town- Silver alloy, town-copper alloy, magnesium alloy, town_indium alloy, Ming, Ming-oxide alloy, | g-Li alloy, indium, about, and materials exemplified in Qiu A 499,011, such as conductive polymers For example, polyrole, polythiophene, polyaniline, polyacetylene, and the like. Preferably, lithium, the word, the town, the indium, the silver, the aluminum or the above-mentioned adducts and alloys are used. In the case of using a metal or a 20 metal alloy as the electrode material, the electrode may be formed only by a vacuum deposition method. In the case of using a metal or a metal alloy as a material for forming an electrode, electrons may be further formed by a chemical plating method (see, for example, Handbook of Electrochemistry, pages 383_387,

Mazuren, 1985). In the case of using a conductive polymer, the electrode can be produced by 69 2004223 77 by forming a thin film on a substrate provided with a conductive coating in advance by an anodic oxidation polymerization method. As a method for forming the thin film, there are, for example, a vacuum deposition method, a spin coating method, a casting method, a Langmuir-Blodgett ("LB") method, an inkjet 5 printing method, and the like. Among these methods, the vacuum deposition method, spin coating method, inkjet printing method, and casting method are particularly excellent in terms of ease of operation and cost. In the case where these layers are formed by using a spin coating method, a casting method, and an inkjet printing method, the coating can be used by dissolving the composition in an appropriate organic solvent (such as benzene, Toluene, xylene, tetra- 10-hydrofuran, methyltetrahydrofuran, N, N-dimethylamidamine, dichloromethane, dimethylsulfoxide, etc.) are implemented. The organic electroluminescence device of the present invention has significant industrial value because it can be used in a flat panel display, a flat light emitting device, a light source of a photocopier or a printer, a liquid crystal display or a light source for a sign, a display signal, etc. No. 15 board and signal lights. The polymer and composition of the present invention can be used in the fields of organic electroluminescence devices, photovoltaic devices, photoreceptors for electrophotography, photoelectric converters, solar cells, image sensors, and the like. Embodiment 3 The following examples are included for illustrative purposes only and are not intended to limit the scope of patent application. Unless otherwise indicated, all parts and percentages are by weight. Example 1 70 200422377

Bis (1,5-cyclooctadiene) nickel (0) (2.0 g, 7.27 mmol) and 2,2, -bipyridyl (1.14 g, 7.27 mmol) were dissolved in anhydrous Toluene (70 liters) and stirred under an argon atmosphere at 80 ° C for 1 hour in the dark. Monomer 1 (0.85 g, ι · 82 5 zemol) and —Yan-9,9-dihexylgoro (0.89 g, 1.82 zemol) were dissolved in anhydrous toluene (7.0 ml), and After being sufficiently purged with argon, it was added to the solution of the Ni complex and stirred for 17 hours under an argon atmosphere at 80 ° C in the dark. Anhydrous toluene (7.0 mL) was added, and the reaction was further performed for 5 hours. Bromobenzene (i mL, 9.5 mmol) was added and the reaction was stirred for a further 2 hours. Reaction 10 The mixture was poured into stirred methanol / c.HCl (aq) (10: 1,600 ml), and the formed precipitate was stirred for 30 minutes and collected by filtration. The precipitate was redissolved in toluene (80 ml) and the precipitation was repeated in acidic methanol. The precipitate was redissolved in chloroform (80 mL), passed through a silica plug, and then washed thoroughly with chloroform (5 X 100 mL). The combined chloroform phases were collected to about 80 ml, and the methanol (600 ml) was stirred at 15 ° C to precipitate and stirred for 30 minutes. The polymer was collected by filtration and dried. 0 · 674 g; 58% material recovery; Mw = 650,000, PD = 2.2. The polymerization reaction of Example 1 can be used to make high from the following monomer families 71 2004 223 77

Mw homopolymer or high Mw statistical copolymer: monomer〗 monomer 2

Polymer Ατι Ar2 Ar3 Rioi 1 phenyl 4-bromophenyl 4-bromophenyl n-hexyl 2 phenyl 4-bromophenyl 4 'bromobiphenyl n-hexyl 3 phenyl 4; bromobiphenyl 4' bromo Phenyl n-hexyl 4 phenyl 4-bromophenyl 4- > styrenyl n-hexyl 5 phenyl 4-benzyl 4 'bromobiphenyl n-hexyl 6 phenyl 4' bromobiphenyl 4 'bromobi Phenyl n-hexyl 7 phenyl 4-bromophenyl 4-benzyl n-octyl 8 phenyl 4-bromophenyl 4 'bromobiphenyl n-octyl 9 phenyl 4' bromobiphenyl 4 '> Biphenyl n-octyl 10 4-Third-butylphenyl 4-bromophenyl 4- '; Biphenyl n-hexyl 11 4-Third-butylphenyl 4-Methyl 4'-Methyl N-hexyl 12 4-tert-butylphenyl 4'bromobiphenyl 4'bromobiphenyl n-hexyl 13 4-tert-butylphenyl 4-bromophenyl 4-benzyl n-heptyl 14 4- Tertiary butylphenyl 4-bromophenyl 4 'bromobiphenyl n-heptyl 15 4-tertiary butylphenyl 4' bromobiphenyl 4 'mobiphenyl n-heptyl 16 4-tert-butyl 4-phenylphenyl 4-bromophenyl 4-bromophenyl n-octyl 17 4-third butylphenyl 4-bromophenyl 4 'bromobiphenyl n-octyl 18 4-third Phenyl 4 'bromobiphenyl 4' mobiphenyl n-octyl 19 4-hexylphenyl 4-bromophenyl 4-mophenyl n-hexyl 20 4-hexylphenyl 4-bromophenyl 4 'bromo Biphenyl n-hexyl 21 4-hexylphenyl 4 'mobiphenyl 4' bromobiphenyl n-hexyl 22 4-hexylphenyl 4-benzyl 4-benzyl n-heptyl 23 4-hexylphenyl 4-bromophenyl 4 'bromobiphenyl n-heptyl 24 4-hexylphenyl 4' bromobiphenyl 4 'bromobiphenyl n-heptyl 25 4-hexylphenyl 4-bromophenyl 4-bromobenzene N-octyl 26 4-hexylphenyl 4-bromophenyl 4 'mobiphenyl n-octyl 27 4-hexylphenyl 4' bromobiphenyl 4 '> stilbyl n-octyl 72 28 4 -Third butyl biphenyl 4-bromophenyl 4-bromophenyl n-hexyl 29 4- Third butyl biphenyl 4-bromophenyl 4 'bromobiphenyl n-hexyl 30 4- third butyl Biphenyl 4 ′ Bromobiphenyl 4 ′ Mobiphenyl n-hexyl 31 4 · Third-butylbiphenyl 4- Mophenyl 4-bromophenyl n-heptyl 32 4-Third-butylbiphenyl 4-bromophenyl 4 'bromobiphenyl n-heptyl 33 4-tert-butylbiphenyl 4' bromobiphenyl 4 'bromobiphenyl n-heptyl 34 4-ter Biphenyl 4- > Oxyphenyl 4- > Oxyphenyl n-octyl 35 4-Third-butylbiphenyl 4-Bromophenyl 4'bromobiphenyl n-octyl 36 4-Third Butylbiphenyl 4'bromobiphenyl 4'bromobiphenyl n-octyl 37 biphenyl 4-bromophenyl 4-bromophenyl n-hexyl 38 biphenyl 4-benzyl 4 'bromobiphenyl N-hexyl 39 biphenyl 4 'mobiphenyl 4' bromobiphenyl n-hexyl 40 biphenyl 4-bromophenyl 4-bromophenyl n-heptyl 41 biphenyl 4-bromophenyl 4 'bromo Biphenyl n-heptyl 42 biphenyl 4 'bromobiphenyl 4' mobiphenyl n-heptyl 43 biphenyl 4-bromophenyl 4-mophenyl n-octyl 44 biphenyl 4-bromobenzene 4 'bromobiphenyl n-octyl 45 biphenyl 4' bromobiphenyl 4 'bromobiphenyl n-octyl 46 2-naphthyl 4-bromophenylfluorene 4-bromophenyl n-hexyl 47 2-naphthalene 4-Methenyl 4'bromobiphenyl n-hexyl 48 2-Qinyl 4'bromobiphenyl 4 'Moth biphenyl n-hexyl 49 2-Qinyl 4-bromophenyl 4-mothyl n-heptyl 50 2-naphthyl 4-bromophenyl 4 'bromobiphenyl n-heptyl 51 2-naphthyl 4' bromobiphenyl 4 'bromobiphenyl n-heptyl 52 2-pentyl 4- Phenyl 4-benzyl n-octyl 53 2-pentyl 4-benzyl 4 'bromobiphenyl n-octyl 54 2-benzyl 4' bromobiphenyl 4 'bromobiphenyl n-octyl 55 3,4-dibutoxy-phenyl 4-bromophenyl 4-bromophenyl_ι) 56 3,4-dioctyloxy-phenyl 4-bromophenyl 4-bromophenyl-1) 57 3,4-Didecoxyphenyl 4-bromophenyl 4-bromophenyl J) υ homopolymer; monomer-free 2 2004 223 77 Example 2 73 2004 223 77

Monomer 1 (1.0 g, 2.15 mmol) and Monomer 3 (138 g, 2.15 mmol) were suspended in toluene (15 ¾ liters), and fully bubbled with argon for 10 minutes. A palladium catalyst (1 mole%) was added, and the toluene phase was further removed for 10 minutes and 5 minutes. Tetraethylammonium hydroxide (20 ° /. Aqueous solution; 8 ml) was added, and the whole was heated under reflux for 20 hours. Bromobenzene (0.2 ml) was added, and the reaction was further performed for 1 hour, then, phenylboronic acid was added, and the reaction was stirred for an additional hour. Upon cooling, the reaction mixture was diluted with toluene (20 mL) and poured into acidic methanol (10 mL of 32% HCl (aq) in 500 mL of MeOH) and filtered. The pale solid was dissolved again in CHC13 (100 ml), filtered through a silica plug (3 cm), and then washed thoroughly with CHC13 (500 ml). CHC13 was removed and the residue was redissolved in toluene (100 ml) and stirred vigorously with a disodium EDTA aqueous solution (5%, 200 ml) for 1 hour. The toluene phase was separated, concentrated to about 50 ml, and precipitated in MeOH (400 ml), filtered and dried. 875mg, 15 79% recovery. The polymerization of Example 2 can be used to make alternating copolymers of the following monomer families: 74 2004 223 77 Monomer 1 Monomer 3

R | 〇1 R101 Polymer M Ar2 Ar3 RlOl 58 Phenyl 4-benzyl 4-benzyl n-hexyl 59 Phenyl 4-bromophenyl 4'bromobiphenyl n-hexyl 60 Phenyl 4 'bromide Biphenyl 4 '> Obiphenyl n-hexyl 61 phenyl 4-Methylphenyl 4-Methylphenyl n-heptyl 62 Phenyl 4- > Obiphenyl 4' Bromobiphenyl n-heptyl 63 Benzene 4 'bromobiphenyl 4' bromobiphenyl n-heptyl 64 phenyl 4-bromophenyl 4-benzyl n-octyl 65 phenyl 4-bromophenyl 4 'bromobiphenyl n-octyl 66 Phenyl 4 'bromobiphenyl 4' bromobiphenyl n-octyl 67 4-Third-butylphenyl 4-Amophenyl 4-Amophenyl-n-hexyl 68 4-Third-butylphenyl 4-Bromo Phenyl 4 'bromobiphenyl n-hexyl 69 4-third butylphenyl 4' bromobiphenyl 4 'bromobiphenyl n-hexyl 70 4-third butylphenyl 4-benzyl 4-benzyl Phenyl n-heptyl 71 4-Third-butylphenyl 4- > Styryl 4 'bromobiphenyl n-heptyl 72 4-Third-butylphenyl 4' bromobiphenyl 4 'bromobiphenyl N-heptyl 73 4-tert-butylphenyl 4-benzyl 4-benzyl-n-octyl 74 4-tert-butylphenyl 4-bromophenyl 4 'bromobiphenyl Octyl 75 4-Third-butylphenyl 4'bromobiphenyl 4'bromobiphenyl n-octyl 76 4-hexylphenyl 4-benzyl 4-benzyl-n-hexyl 77 4-hexylphenyl 4-bromophenyl 4 'bromobiphenyl n-hexyl 78 4-hexylphenyl 4' bromobiphenyl 4 'bromobiphenyl n-hexyl 79 4-hexylphenyl 4-bromophenyl 4-benzyl n- Heptyl 80 4-hexylphenyl 4-benzyl 4 'bromobiphenyl n-heptyl 81 4-hexylphenyl 4' bromobiphenyl 4 'bromobiphenyl n-heptyl 82 4-hexylphenyl 4 -Bromophenyl 4- > Styrenyl n-octyl 83 4-hexylphenyl 4-bromophenyl 4 'bromobiphenyl n-octyl 84 4-hexylphenyl 4' mobiphenyl 4 'bromobi Phenyl n-octyl 85 4-tert-butylbiphenyl 4-bromophenyl 4-bromophenyl-n-hexyl 75 2004223 77 86 4-tert-butylbiphenyl 4-bromophenyl 4'bromobiphenyl N-hexyl 87 4-tert-butylbiphenyl 4'bromobiphenyl 4'bromobiphenyl n-hexyl 88 4-tert-butylbiphenyl 4- > styrenyl 4-bromophenyl n- Heptyl 89 4-Third-butylbiphenyl 4-mophenyl 4'bromobiphenyl n-heptyl90 4-Third-butylbiphenyl 4'Mobiphenyl 4 ' Bromobiphenyl n-heptyl 91 4-tert-butylbiphenyl 4-benzyl 4- > Styrenyl n-octyl 92 4-tert-butylbiphenyl 4-bromophenyl 4'bromo Biphenyl n-octyl 93 4-Third-butylbiphenyl 4 'Mobiphenyl 4' Bromobiphenyl n-octyl 94 Biphenyl 4-bromophenyl 4-bromophenyl n-hexyl 95 Biphenyl 4-Methenyl 4'bromobiphenyl n-hexyl 96 biphenyl 4'bromobiphenyl 4'bromobiphenyl n-hexyl 97 biphenyl 4-bromophenyl 4-bromophenyl n-heptyl 98 Biphenyl 4-benzyl 4'bromobiphenyl n-heptyl 99 biphenyl 4'bromobiphenyl 4'bromobiphenyl n-heptyl 100 biphenyl 4-benzyl 4-bromophenyl N-octyl 101 biphenyl 4- > odorant 4 'bromobiphenyl n-octyl 102 biphenyl 4' mobiphenyl 4 'bromobiphenyl n-octyl 103 2-naphthyl 4-bromo Phenyl 4- > Styrenyl n-hexyl 104 2-Qinyl 4-benzyl 4 'bromobiphenyl n-hexyl 105 2-Qinyl 4' molyl 4phenyl molyl n-hexyl 106 2 -Qinyl 4-benzyl 4-bromophenyl n-heptyl 107 2-Qinyl 4- > Styrenyl 4 '> Stylenyl biphenyl n-heptyl 108 2-naphthyl 4 Bromobiphenyl 4 'bromobiphenyl n-heptyl 109 2-Qinyl 4- > Styryl 4-bromophenyl n-octyl 110 2-Qinyl 4' bromobiphenyl 4 'bromobiphenyl N-octyl 111 2-naphthyl 4 'bromobiphenyl 4' bromobiphenyl n-octyl Example 3 I II J Ni (COD) 2 J 2,2_-pyridinedipyridine M-, ^ ϊιΜ benzene 80BC. r CrBr

Monomer 3

76 200422377 Bis (1,5_cyclooctadiene) nickel (0) (2.0 g, 7.27 mmol) and 2,2, dibiidine (1.14 g, 7.27 ¾ mole) were dissolved in anhydrous toluene (7.0 Torr), and stirred in the dark at 80 ° C under an argon atmosphere for 1 hour. Monomer 3 (2.38 grams, 3.3 millimoles) was dissolved in anhydrous toluene (70 mL and fully purged with argon), and then 5 was added to the Nl complex solution at 80 ° in the dark Stir under C argon for 17 hours. Anhydrous toluene (7.0 mL) was added and the reaction proceeded for another 5 hours. Bromobenzene (1 mL, 9.5 mmol) was added and the reaction was stirred for another 2 hours. The reaction mixture was poured to Stirred in methanol / c.HCl ^ (10: 1,600 ml), and the formed precipitate was stirred for 30 minutes and collected by filtration. The precipitate was again dissolved in toluene (80 ml), And the precipitation in acidic methanol was repeated. The precipitate was dissolved again in aeroform (80 ml), passed through a silica plug, and then thoroughly washed with aeroform (5 x 100 ml). The mixed aeroform phase It was concentrated to about 80 ml and precipitated in stirred methanol (600 ml) and stirred for 30 minutes. The polymer was collected by filtration and dried. 15 Example 4

Single «4 Monomer 4 (5.0 g, 14.95 mmol), AIBN (48 mg, 0.293 mmol) and chlorobenzene (12 g) were purged with argon and then heated to 150 ° C in an argon atmosphere 20 and Lasts 2 hours. The hot solution was poured into stirred methanol (300 ml) and the white precipitate formed was filtered. The precipitate was redissolved in toluene (60 mmol 77 2004 223 77 liters) and slowly dropped into an acidic methanol solution (2 ml of c.HCl in 400 ml of MeOH). The polymer was filtered, washed with methanol and dried overnight at 40 ° C under vacuum. Mass = 3.5 grams, 70% of material recovered; Mw = 20,000 (GPC, PS standard). 5 Example 5

Bis (1,5-cyclooctadiene) nickel (0) (2.0 g, 7.27 mmol) and 2,2'-bipyridine (1.14 g, 7.27 mmol) were dissolved in anhydrous toluene (7.0 ml) ) And stirred in a dark 10 at 8 (TC argon atmosphere for 1 hour. Monomer 5 (2.38 g, 3.3 mmol) was dissolved in anhydrous toluene (7.0 ml) and fully removed with argon, and then added to The Ni complex solution was stirred in the dark under argon at 80 ° C for 17 hours. Anhydrous toluene (7.0 mL) was added, and the reaction was further performed for 5 hours. Bromobenzene (1 mL, 9.5 mmol) was added And the reaction was further stirred for 2 hours. 15 The reaction mixture was poured into a stirred formic acid / c.HCl (aq) (10: 1,600 ml), and the formed precipitate was stirred for 30 minutes and collected by filtration. The precipitate was redissolved in toluene (80 ml) and the precipitation in acidic methanol was repeated. The precipitate was redissolved in chloroform (80 ml) and passed through a silica plug, then chloroform (5 X 100 ml) Wash thoroughly. The mixed chloroform phase was reduced to about 80 ml by concentrated 78 200422377, and precipitated in stirred methanol (600 ml), and stirred for 30 minutes. Bell. The polymer was collected by filtration and dried. Example 6

5 Monomer 6 (2.0 g, 3.65 mmol) and Monomer 7 (1.38 g, 3.65 mmol) were suspended in toluene (15 mL) and fully purged with bubble argon 1 〇minutes. A palladium catalyst (1 mole%) was added, and the toluene phase was further removed for 10 minutes. Tetraethylammonium hydroxide (20% aqueous solution; 14 ml) was added, and the whole was heated to reflux for 20 hours. Bromobenzene (0.2 ml) was added, and the reaction was further performed for one hour, then, phenylboronic acid was added, and the reaction was disturbed for another hour. Upon cooling, the reaction mixture was diluted with toluene (20 mL) and poured into acidic methanol (10 mL of 32% HCl (aq) in 500 mL of MeOH) and filtered. The pale solid was re-dissolved in toluene (100 mL) and stirred vigorously with disodium EDTA 15 aqueous solution (5%, 200 mL) for 1 hour. The toluene phase was separated, concentrated to about 50 ml, and precipitated in MeOH (400 ml), filtered and dried. Example 7 79 2004 223 77

Monomer 6 (2.0 g, 3.65 mmol) and Monomer 7 (1.98 g, 3.65 mmol) were suspended in toluene (15 ml) and thoroughly purged with bubble argon for 10 minutes. The catalyst (1 mole%) was added and the toluene phase was further removed for 10 minutes. Tetraethylammonium hydroxide (20% aqueous solution; 14 ml) was added, and the whole was heated under reflux for 20 hours. Bromobenzene (0.2 ml) was added, and the reaction was further performed for one hour, then, phenylboronic acid was added, and the reaction was stirred for an additional hour. Upon cooling, the reaction mixture was diluted with toluene (20 mL) and poured into acidic methanol (10 mL of 32% HCl (aq) in 500 mL of MeOH) and filtered. The pale solid was dissolved again in toluene (100 mL) and was vigorously stirred with disodium EDTA aqueous solution (5%, 200 mL) for 1 hour. The toluene phase was separated, concentrated to about 50 ml, and precipitated in MeOH (400 ml), filtered and dried. Application Example 1 ITO-glass for device manufacturing has a nominal sheet resistance of 12 ohms / square. Electron hole ejection conductive polymer is poly (3,4-ethylene dioxy-benzene) (PEDT) when used, and electron hole transporting polymer is poly (4,4, _ 80 2004223 77) Biphenyl-diyl-N'N'-diphenyldiamino-1,4-phenylene) (which is described in US-B-5,728,801, and abbreviated as " P3DA "), and the electron The transport layer, when used, is an aluminum complex of 8-hydroxy-pyridoline, and is abbreviated as "Alq" hereinafter. The PEDT film was formed by spin coating of an aqueous polymer solution obtained from Bayer. The P3DA film is formed by spin coating of a chlorobenzene solution. The Alq film is formed by thermal evaporation in a high vacuum. Multilayer devices are made by sequentially laying out these layers, starting with the layer adjacent to ITO. After all the layers have been deposited, a suitable metal cathode is deposited on the organic film by thermal evaporation. The magnesium alloy in this example is a magnesium alloy containing at least 85% magnesium. The living polymer is deposited by spin coating from an organic solvent (toluene). Electroluminescent device device number Electron hole ejection electron hole transport polymer Electron transport cathode D1-64-Mg alloy D2--64 Alq "D3-P3DA 64-" D4-P3DA 64 Alq "D5 PEDT PVK 64-A1 D6-PVK 64-A11) D7 PEDT-64-A11) υ A thin layer of calcium or barium (approximately 5 nm) exists between the electron transport layer and the cathode; PVK = polyvinylcarbazole. 15 [Simplified illustration of the drawing] ( [None] [Representation of the main symbols of the diagram] (None) 81

Claims (1)

2004223 77 Scope of patent application: 1. A polymer containing repeating units of the following chemical formula (I), special department Alas, (II), special department (Ila), (Ilb), or (lie); wherein R1, R2, R3, R4 and R5 are each an organic substituent, especially a C2-C30 aryl group or a C2-C26 heteroaryl group, which may be optionally substituted, 82 2004223 77 X1, X2 and X3 are each a divalent bond group. 2. The polymer according to item 1 of the scope of patent application, wherein X1 and X2 are each independently a base of the following chemical formula, R14 ’r14_ , Or three-, special department 83 200422377 Among them, nl, n2, n3, n4, n5, n6 and n7 are integers from 1 to 丨 0, especially from i to 5 3, 10 R6 and R7 are each H, CrC18 alkyl, CVCm substituted with E and / or d interrupted, CrCi2 cycloalkyl, C5_C12 cycloalkyl substituted with e, C6-C24 aryl, and E substituted c6_C24 aryl, (^ (^ heteroaryl, C2-C20 heteroaryl substituted with E, C2-C18 dilute, c2-C18 fastyl, CrC18 alkoxy, substituted with E and / or interrupted by D (^ _ (: 18 alkoxy, C7_C25 aralkyl, or -CO-R28, R8 CrCls alkyl, CrC18 alkyl substituted with E and / or D interrupted, C6-C24 aryl, or (: 7- ( : 25 aralkyl, 84 15 2004 223 77 R9 and R1G are each CrC18 alkyl, substituted with E and / or D interrupted CrC18 alkyl, C6_C24 aryl, E substituted C6_C24 aryl, C2-C20 hetero Aryl, C2-C2 () heteroaryl substituted with E, C2-C18 alkenyl, 02-018 alkynyl, CrC18 alkoxy, CVC18 alkoxy 5 substituted with E and / or D interrupted, or C7-C25 aralkyl, or R9 and R1G form a ring, especially a five- or six-membered ring, which can be optionally substituted by R6, R14 'and R15' are each H, CrC18 alkyl, and E Substituted and / or D interrupted CrC18 alkyl, C6-C24 aryl, E substituted C6-C24 aryl, 10 C2-C2G heteroaryl, or C2-C2 substituted with E. Heteroaryl, D is -CO-; -COO-; -S-; -SO-; -S02 ·; 0 -; -NR25 ·; -SiR3〇R31-; -POR32 ·; -CR23 = CR24-; or -OC-; and E system -OR29; -SR29; -NR25R26; -COR28; -COOR27; -CONR25R26; -CN -OCOOR27; or halogen; wherein, 15 R23, R24, R25 and R26 are each H; C6_C18 aryl; C6-C18 aryl substituted with (^ _ (8 alkyl, CrC18 alkoxy); CrC18 Group; or Cr-C18 alkyl group with 0-interruption; or R25 and R26 together form a ring of five or six members, especially 20 R27 and R28 are each H; C6-C18 aryl; C6-C1S aryl substituted with CrC18 alkyl, or 85 2004223 77 CVC18 alkoxy; Ci_Cl8 alkyl; or -0-intermittent Crc18 Alkyl, R29 is H; C6-C18 aryl; c6-c18 aryl substituted with CVC 8 alkyl, crcis alkoxy; crc18 alkyl; or intermittent CrCl8 alkyl, 5 R3 ° and R31 each other Some are crC18 alkyl, c6-ci8 aryl, or C6-C18 aryl substituted with Ci_Ci8 alkyl, and R32 is CVC18 alkyl, C6-C18 aryl, or C6_C18 aryl substituted with CrC18 alkyl. 3. The polymer as described in item 1 or 2 of the scope of patent application, wherein R1 and 10 R2 are each H, ci_C18 alkyl, substituted with E and / or D interrupted CrC18 alkyl, c2-Cl8 ene , C2_Ci8 alkynyl, Cl. Alkoxy, substituted by e R 14 · R14 and / or c-c μ alkoxy interrupted by D, R X4 > -R15, 15 ·, X4--X5 C7-C25 aryl, cc optionally Is substituted, _ is as follows or C2 'heteroaryl, which is selected 15 86 2004 223 77 87 2004223 77 Special series 1 to 3, X6 series H, CrCu sintered group, substituted with E and / or D intermittent CrCu sintered R11 ~ ^ R12 group, CrC% aryl group, which can be optionally substituted, especially R13, , CrC18 alkynyl, CrC18 alkoxy, CrC18 alkoxy substituted with E and / or D interrupted, or C7-C25 * alkyl, X4 CVCm alkyl substituted with E and / or D interrupted crc18 alkyl, C6-C24 aryl, which can be optionally substituted, 10 X5 C1_C18 alkyl, C6_C24 aryl, noccr18 substituted C6-C24 square or -OC6-C24 aryl, R11 , R12 and R13 are each H, CrC18 alkyl, CrC18 alkyl substituted with E and / or D interrupted, C6-C24 aryl, C6_C24 aryl substituted with e, CrC18 alkenyl, C2-C18 alkynyl , CrC18 alkoxy, CrC, 8 alkoxy, or crc25 aralkyl substituted with E and / 15 or D, and D, E, R6, R 'R8, R9, R' rm '& r15 'As defined in item 2 of the scope of patent application. 4. The polymer as described in any one of claims 1 to 3, comprising 88 2004223 77 comonomer τ, which is selected from the group consisting of 89 2004 223 77 R16 is H; C6-C18 aryl, C6_C18 aryl substituted with CrC18 alkyl, CrC18 alkyl, C7-C25 aralkyl, or -0-interrupted CrC18 alkyl; p is an integer from 1 to 10, Special 1,2 or 3, 10 q is an integer from 1 to 10, especially 1,2 or 3, 90 200422377 s is an integer from 1 to 10, especially 12 4 3, 110, 117, 118, 119 and 111 () Is as defined in item 2 of the scope of patent application, or R9 and R1G together form a five- or six-membered ring, which is replaced by R6, R9 and R10 together form the base of chemical formula = CR10〇R101, of which 5 RlGG and RlG1 are each H, CrC18 alkyl, CVCu alkyl substituted with e and / or D interrupted, CVCm aryl, C6-C24 aryl substituted with e, G-C2. Heteroaryl, or C2-C2G heteroaryl substituted with E, and R14 and R15 are each H, CVCu alkyl, substituted with e and / or D interrupted CrC18 alkyl, C6-C24 aryl, to E-substituted c6-C24 aryl, C2-C20 hetero10 aryl, or E-substituted C2-C2G heteroaryl. 5. The polymer according to any one of claims 1 to 3 of the patent application scope, comprising a repeating unit of chemical formula la or lb, wherein ri is the base of the following chemical formula Among them, R2 is H, R6 and R7 are each H, CVCu alkyl, CVCu cycloalkyl, especially cyclohexyl, CVC24 aryl, especially phenyl, naphthyl or biphenyl, which may be _〇_CrC12 Alkyl or CrC18 alkoxy substituted, 91 2004223 77 R8 CrCls alkyl, Ci_Ci8 alkyl interrupted by one or two oxygen atoms, or q-q2 aryl, which may optionally be substituted by CrCi2 alkyl, or Ci_Ci2 Alkoxy substitution, R9 and R1G are each H, crc12 alkyl, or 〇1_〇: 12 alkoxy, 5 are 9 and R1G each are crci8 alkyl, especially C4-C12 alkyl, which can be One or two oxygen atoms are discontinuous, and X1 and X2 are as defined in item 1 of the scope of patent application. 6. The polymer as described in item 5 of the scope of patent application, including a co-monomer τ, which is selected from the group consisting of 92 2004 223 77 Now R, or 〇, where ^ is Crc18 alkyl, R9 and R1G are each independently (VC! 8 alkyl group, especially cvc12 alkyl group, which may be interrupted by one or two oxygen atoms, or R9 and R1G may form a five- or six-membered carbocyclic ring, which may optionally be crC8 alkyl group substitution. 7. The polymer described in item 1 of the scope of patent application, including repeating units of the following chemical formula Co-monomer y, where X is in the range of 0.0 () 5 to 1, especially G 4 to G 6, and y is in the range of G 995 to 0, especially 0.6 to 0.4, where the sum of χ and y is 1 R1 is the base of the formula '93 2004 223 77 Among them, X6 is H, CrCls, alkyl, cyclohexyl, or Ci_Ci8 alkoxy, R2 is H, and 5 X1 and X2 are each a group of the following chemical formula. τ series chemical formula Base, where S is 1 or 2, and R9 And R1G are each CrCls alkyl, especially c4-Cl2 alkyl, which can be interrupted by 10 or two oxygen atoms, and R6 and R7 are each H, CrC12 alkyl, C5-C12 cycloalkyl, such as, Cyclohexyl, C6-C24 aryl, especially phenyl, naphthyl, or biphenyl, which can be substituted with ―0-crc12 alkyl, or cvc18 alkoxy. 8. The polymer as described in item 1 of the scope of the patent application, which includes a repeating unit of the formula Ila, 15 IIb4Hc, wherein X3 is the base of the following formula 94 2004223 77 R71 Among them, the dashed line indicates the bond to the pyrimidine ring, R3, R4, and R5 are as defined in the scope of the first patent application, 5 R56 and R57 are each H; CrC18 alkyl; substituted with E and / or D interrupted CrC18 alkyl; C5-C12 cycloalkyl, substituted with E (: 5-0: 12 cycloalkyl, C6-C24 aryl; C6-C24 aryl substituted with E; C2-C2G heteroaryl C2-C2 () heteroaryl substituted with E; C2-C18 alkenyl; C2-C18 alkynyl; CrC18 alkoxy; substituted with E and / or D interrupted by (^ 忑 18alkoxy; or C7 -C25 10 aralkyl; R58 is H; CrC18 alkyl; CrC18 alkyl substituted with E and / or D interrupted; C6-C24 aryl; or C7-C25 aralkyl; R59 is H; C "C18 Alkyl; substituted with E and / or interrupted by D (^ -0: 18 alkyl; C6-C24 aryl; C6-C24 aryl substituted with E; C2-C2G heteroaryl; C2-C2G hetero substituted with 15 E Aryl; C2-C18 alkenyl; C2-C18 alkynyl; (^ _0: 18 alkoxy; substituted with E and / or interrupted by D (^ -0: 18 alkoxy; or C7-C25 aromatic Group; or 95 2004223 77 R59 and R6G form a ring, especially a five or six member ring, R71 is H, CVC18 alkyl, -ON, -CONR25r26 or _ c〇〇r27, D system -CO-; -COO-; -OCOO-; _S_; -S〇-; _s〇2 ·; _nr25_; _ SiR30R31-; -POR32-; -CR23 = CR24-; or CCs and 5 E # -OR29; -SR29; -NR25R26; -COR28; -COOR27; -CONR25R26; -CN; -OCOOR27; or halogen; where R23; R24; R25 and R26 are each independently H; C6-Ci8 aryl; C6-C18 aryl substituted with (^ < 18 alkyl, CVC18 alkoxy; c "C18 alkyl; or -0- Intermittent crc18 alkyl groups; or 10 R25 and R26 together to form a five or six membered ring, especially R27 and R28 are each H; C6-C18 aryl; c6-cl8 aryl substituted with Cl-Cl8 alkyl, or Cr C18 alkoxy; CrC18 alkyl; or -VC1S alkyl And 15 R29 is H; C6-C18 aryl group; cvc18 square group substituted with CrC18 alkyl group and q-Cu alkoxy group; CrC18 alkyl group; or -0 · intermittent CrCn alkyl group, R30 and R31 are separate from each other Is CrC18 alkyl, c6-C18 aryl, or c6-c18 aryl substituted with CrC18 alkyl, and R32 is c "c18 alkyl, C6-C18 aryl, or c6_Ci8 20 aryl substituted with Ci_Ci8 alkyl 9. The polymer as described in item 8 of the scope of the patent application, wherein r3, r4 and R5 are each H, CVCu alkyl, each substituted with e and / or D interrupted 96 2004223 77 CrC18 alkyl, C2 -C18 alkenyl, C2-C18 alkynyl, CrC18 alkoxy, E R64 R65 Substituted and / or D-interrupted (^-(: ^ alkoxy, ^^ χ5, 〇7-〇: 25aralkyl, c6-c24aryl, or c2-c20heteroaryl, the selectivity can be Substituted, especially the base of the formula 97 2004 223 77 5 Among them, ml, m2, m3, m4, m5, m6, and m7 are integers from 1 to 10, especially from 1 to 3, X6 is H, CrCls alkyl, crC18 alkoxy, substituted with E and / or D Discontinuous CrCls group, cvc24 aryl group, which can be optionally substituted, especially 10 R61V R62 h heteroaryl, which may be optionally substituted, in particular, 63 R 56 057 N, C2-C18 dilute group, C2-C18 alkynyl group, (^ -C alkoxy group, CrC18 alkoxy group substituted with E and / or D interruption, or c7_c 18 98 25 2004223 77 aryl group, X4 system CVC18 alkyl, CrC18 alkyl substituted with E and / or D interrupted, C6-C24 aryl or C2-C2Q heteroaryl, which can be optionally substituted, X5 is CrC18 alkyl, C6-C24 aryl , Or C2-C2. Heteroaryl, which may optionally be substituted with -OCrC18 alkyl or -OC6-C24 aryl, R61, R62 and R63 are each H, CrC18 alkyl, CrC18 alkyl substituted with E and / or D interrupted, C6-C24 aryl, C6-C24 aryl substituted with E, C2-C18 alkenyl, C2-C18 alkynyl, CrC18 alkoxy, CrC18 alkoxy substituted with D and / or D interrupted, or C7-C25 aralkyl, 10 R64 and R65 are each H, CVC18 alkyl, substituted with E And / or CrC18 alkyl interrupted by D, C6-C24 aryl, C6-C24 aryl substituted by E, or C2-C2. Heteroaryl, C2-C2G heteroaryl substituted with E, and D, E, R56, R57, R58, R59 and R6G are as defined in item 8 of the scope of patent application. 15 10. The polymer according to item 8 or 9 of the scope of patent application, including comonomers T, which is selected from the group consisting of 99 2004 223 77 100 2004 223 77 5 Among them, P is an integer from 1 to ίο, especially 1, 2, or 3, q is an integer from 1 to 10, especially 1, 2 or 3, S is an integer from 1 to 10, and particularly 1, 2, or 3 , R72 is H; C6-C18 aryl; C6-C18 aryl with 10 substituted by CrC18 alkyl or Ci_Ci8 alkoxy; crC18 alkyl; Ci_Ci8 alkyl interrupted by -0_; RW, R59, R6〇, ㊇ and R65 are as defined in item 8 of the scope of the patent application, or R59 and R60 together form the base of the chemical formula, wherein R and R1 () 1 are each independently H, a radical, substituted with E and / or interrupted by d 101 2004223 77 CrC18 alkyl, C6-C24 aryl, C6-C24 aryl substituted with E, or C2-C20 heteroaryl, or C2-C2Q heteroaryl substituted with E, where D and E are as As defined in item 8 of the scope of patent application. 11. The polymer according to any one of items 8 to 10 of the scope of patent application, including 5 repeating units containing the chemical formula lib, especially repeating units of the chemical formula Ila or lie, and comonomer T, wherein X3 is Chemical formula Base, wherein the dotted line represents a bond to the pyrimidine ring, and R71 is H, alkyl, -ON, or -COOR27, wherein R27 is H, or alkyl, which may optionally have one or two oxygen atoms Discontinued, 10 is especially c4-c12 alkyl, which can optionally be interrupted by one or two oxygen atoms, 15 Among them, R59 and R6G are each CVC18 alkyl group, especially C4-C12 alkyl group, 102 2004 223 77 It can be interrupted by one or two oxygen atoms. 12. An optical device or a component thereof, comprising a substrate and a polymer according to any one of claims 1 to 11 of the patent application. 5 13. The optical device according to item 12 of the scope of patent application, wherein the optical device includes an electroluminescent device. 14. The optical device according to item 13 of the scope of patent application, wherein the electroluminescent device includes (a) a charge ejection layer for ejecting a positive charge carrier, and 10 (b) an ejection charge for a negative charge carrier A spray layer, (c) a light-emitting layer located between the rhenium and (b) layers, which comprises the polymer as described in any one of the claims 1 to 11 of the patent application scope. 15. —A monomer with the following chemical formula X11-a X1 15 (Ilia), or (mb); and / or 103 2004223 77 J-x3-:-X11 (IV), particularly the winter '(IVa), " (IVb), or "(IVc); wherein 5 R1, R2, R3, R4 and R5 are each an organic substituent, especially a crc30 aryl or a c2-c26 heteroaryl, which may be optionally substituted, X1, X2, and X3 are each a divalent bond group, and X11 is a halogen atom in each case, or _B (0H) 2, -B (〇Yl) 2, or '< > 2 5 10 Among them, γ1 is a CrC1G alkyl group in each case, and Y2 is a C2_C1G alkyl group in each case, such as _CY3Y4_CY5Y6 •, or — CY7Y8-CY9Y10_ CYUY1, where Υ3, Υ4, γ5, γ6, γ7, γ8, γ9 Υ, Υ, and Υ are each hydrogen or CrC1 () alkyl group, in particular _C (CH3) 2C (CH3) 2-, or -C (CH3) 2CH2C (CH3) 2_, but with the condition 104 2004223 77 2-Phenyl-4,6-bis (p-bromophenyl) pyrimidine and 2,4,6-tri (p-bromophenyl) pyrimidine were excluded. 105 2004223 77 (1) Designated representative map: (1) The designated representative map in this case is: (). (2) Brief description of the component representative symbols of this representative map: (none) 捌 If there is a chemical formula in this case, please disclose the chemical formula that can best show the characteristics of the invention: 4